Composite material, light-emitting element, light-emitting device, electronic device, and lighting device

ABSTRACT

A composite material which includes an organic compound and an inorganic compound and has a high carrier-transport property is provided. A composite material having a good property of carrier injection into an organic compound is provided. A composite material in which light absorption due to charge-transfer interaction is unlikely to occur is provided. A composite material having a high visible-light-transmitting property is provided. A composite material including a hydrocarbon compound and an inorganic compound exhibiting an electron-accepting property with respect to the hydrocarbon compound is provided. The hydrocarbon compound has a substituent bonded to a naphthalene skeleton, a phenanthrene skeleton, or a triphenylene skeleton and has a molecular weight of 350 to 2000, and the substituent has one or more rings selected from a benzene ring, a naphthalene ring, a phenanthrene ring, and a triphenylene ring.

BACKGROUND OF THE INVENTION 1. Field of the Invention

The present invention relates to a composite material including anorganic compound and an inorganic compound, a light-emitting element, alight-emitting device, an electronic device, and a lighting device.

2. Description of the Related Art

In recent years, research and development have been extensivelyconducted on light-emitting elements using organic electroluminescence(EL). In a basic structure of such a light-emitting element, a layercontaining a light-emitting organic compound is interposed between apair of electrodes. By application of a voltage to this element, lightemission from the light-emitting organic compound can be obtained.

Since such light-emitting elements are of self-light-emitting type, itis considered that the light-emitting elements have advantages overliquid crystal displays in that visibility of pixels is high, backlightsare not required, and so on and are therefore suitable as flat paneldisplay elements. In addition, it is also a great advantage that thelight-emitting elements can be manufactured as thin and lightweightelements. Furthermore, very high speed response is also one of thefeatures of such elements.

Furthermore, since such light-emitting elements can be formed in a filmform, they make it possible to easily form large-area elements. Thisfeature is difficult to obtain with point light sources typified byincandescent lamps and LEDs or linear light sources typified byfluorescent lamps. Thus, light-emitting elements also have greatpotential as planar light sources applicable to lighting devices and thelike.

As described above, application of light-emitting elements using organicEL to light-emitting devices, lighting devices, or the like is expected.At the same time, there are many issues regarding light-emittingelements using organic EL. One of the issues is a reduction in powerconsumption. In order to reduce power consumption, it is important toreduce driving voltage for the light-emitting element. Further, in orderto reduce the driving voltage, it is necessary to feed a large amount ofcurrent at a low voltage because the emission intensity of thelight-emitting element using organic EL is determined by the amount ofelectric current flowing therein.

Previously, as a method for reducing driving voltage, an approach ofproviding a buffer layer between an electrode and the layer containing alight-emitting organic compound, has been attempted. For example, it isknown that driving voltage can be reduced by providing a buffer layerwhich includes polyaniline (PANI) doped with camphorsulfonic acid,between indium tin oxide (ITO) and a light-emitting layer (seeNon-Patent Document 1, for example). It is explained that this isbecause PANI has a property of excellent carrier injection into thelight-emitting layer. Note that in Non-Patent Document 1, PANI, which isused for the buffer layer, is also regarded as part of the electrode.

However, as described in Non-Patent Document 1, PANI has a problem thattransmittance becomes poor when a film thickness becomes thick.Specifically, it is reported that at a film thickness of about 250 nm,the transmittance is less than 70%. In other words, since the problemlies in the transparency of the material itself used for the bufferlayer, light generated within the element cannot be extractedefficiently.

Also, according to Patent Document 1, an approach of serially connectinglight-emitting elements (called light-emitting units in PatentDocument 1) to improve luminance per a certain current density, namely,current efficiency, has been attempted. In Patent Document 1, for aconnecting portion of serially connected light-emitting elements, amixed layer of an organic compound and a metal oxide (specifically,vanadium oxide or rhenium oxide) is used, and this layer is consideredcapable of injecting holes and electrons into light-emitting units.

However, as apparent by looking at an embodiment, for the mixed layer ofan organic compound and a metal oxide which is disclosed in PatentDocument 1, not only a high absorption peak in the infrared region butalso a high absorption peak in the visible light region (around 500 nm)are observed, and a problem in transparency occurs. This is due to theeffect of an absorption band generated by charge-transfer interaction.Therefore, as expected, light generated within the element cannot beextracted efficiently, and the light emission efficiency of the elementis degraded.

REFERENCES

-   [Patent Document 1] Japanese Published Patent Application No.    2003-272860-   [Non-Patent Document 1] Y. Yang et al., Applied Physics Letters,    Vol. 64 (10), 1245-1247 (1994)

SUMMARY OF THE INVENTION

In view of the above description, an object of one embodiment of thepresent invention is to provide a composite material which includes anorganic compound and an inorganic compound and which has a highcarrier-transport property. Another object of one embodiment of thepresent invention is to provide a composite material having a goodproperty of carrier injection into an organic compound. Another objectof one embodiment of the present invention is to provide a compositematerial in which light absorption due to charge-transfer interaction isunlikely to occur. Another object of one embodiment of the presentinvention is to provide a composite material having a highvisible-light-transmitting property.

An object of one embodiment of the present invention is to provide alight-emitting element having high emission efficiency by applying theabove-described composite material to the light-emitting element.Another object of one embodiment of the present invention is to providea light-emitting element having a low driving voltage. Another object ofone embodiment of the present invention is to provide a light-emittingelement having a long lifetime. Another object of one embodiment of thepresent invention is to provide a light-emitting device including thelight-emitting element, an electronic device including thelight-emitting device, or a lighting device including the light-emittingdevice.

Note that an object of the invention to be disclosed below is to achieveat least one of the above-described objects.

One embodiment of the present invention is a composite materialincluding a hydrocarbon compound which has a substituent bonded to anaphthalene skeleton, a phenanthrene skeleton, or a triphenyleneskeleton and which has a molecular weight greater than or equal to 350and less than or equal to 2000, and an inorganic compound exhibiting anelectron-accepting property with respect to the hydrocarbon compound. Inthe hydrocarbon compound, the substituent has one or more rings selectedfrom a benzene ring, a naphthalene ring, a phenanthrene ring, and atriphenylene ring. Note that unless otherwise specified, the ring of thehydrocarbon compound in the composite material of one embodiment of thepresent invention may be a substituted or unsubstituted ring. Forexample, the substituent may have one or more rings selected from asubstituted or unsubstituted benzene ring, a substituted orunsubstituted naphthalene ring, a substituted or unsubstitutedphenanthrene ring, and a substituted or unsubstituted triphenylene ring.

The above-described composite material has a high carrier-transportproperty. The above-described composite material also has a goodproperty of carrier injection into an organic compound. Further, in thecomposite material, light absorption due to charge-transfer interactionis unlikely to occur. Furthermore, the composite material has a highvisible-light-transmitting property (hereinafter simply referred to aslight-transmitting property).

The hydrocarbon compound included in the composite material of oneembodiment of the present invention, which has a substituent bonded to anaphthalene skeleton, a phenanthrene skeleton, or a triphenyleneskeleton (the substituent has one or more rings selected from a benzenering, a naphthalene ring, a phenanthrene ring, and a triphenylene ring)and which has a molecular weight greater than or equal to 350 and lessthan or equal to 2000, exhibits an absorption peak at a shorterwavelength than visible-light wavelengths (380 nm to 760 nm).

In the above composite material, the occurrence of light absorption dueto charge-transfer interaction can be suppressed and an absorption peakof the hydrocarbon compound itself can also be controlled so as toappear at a shorter wavelength than visible-light wavelengths (380 nm to760 nm). Accordingly, the composite material can have a highlight-transmitting property.

A naphthalene skeleton, a phenanthrene skeleton, and a triphenyleneskeleton each have a rigid structure; therefore, the molecular weight ofthe hydrocarbon compound is preferably 350 or more because the filmquality of the composite material is stable with such a molecularweight. More preferably, the molecular weight is 450 or more. Althoughthere is no limitation on the maximum molecular weight, the molecularweight is preferably 2000 or less in consideration of evaporativity whenthe composite material is subjected to heating evaporation.

One embodiment of the present invention is a composite materialincluding a hydrocarbon compound which has a molecular weight greaterthan or equal to 350 and less than or equal to 2000 and which exhibitsan absorption peak at a shorter wavelength than visible-lightwavelengths, and an inorganic compound exhibiting an electron-acceptingproperty with respect to the hydrocarbon compound. In the hydrocarboncompound, a substituent is bonded to a naphthalene skeleton, aphenanthrene skeleton, or a triphenylene skeleton, and the substituenthas one or more rings selected from a benzene ring, a naphthalene ring,a phenanthrene ring, and a triphenylene ring.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound which has a substituent bonded to theα- or β-position of a naphthalene skeleton, the 9-position of aphenanthrene skeleton, or the 2-position of a triphenylene skeleton andwhich has a molecular weight greater than or equal to 350 and less thanor equal to 2000, and an inorganic compound exhibiting anelectron-accepting property with respect to the hydrocarbon compound. Inthe hydrocarbon compound, the substituent has one or more rings selectedfrom a benzene ring, a naphthalene ring, a phenanthrene ring, and atriphenylene ring.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound which has a molecular weight greaterthan or equal to 350 and less than or equal to 2000 and which exhibitsan absorption peak at a shorter wavelength than visible-lightwavelengths, and an inorganic compound exhibiting an electron-acceptingproperty with respect to the hydrocarbon compound. In the hydrocarboncompound, a substituent is bonded to the α- or β-position of anaphthalene skeleton, the 9-position of a phenanthrene skeleton, or the2-position of a triphenylene skeleton, and the substituent has one ormore rings selected from a benzene ring, a naphthalene ring, aphenanthrene ring, and a triphenylene ring.

In the composite material, the occurrence of light absorption due tocharge-transfer interaction can be suppressed by use of the hydrocarboncompound having a substituent at the α- or β-position of a naphthaleneskeleton, the 9-position of a phenanthrene skeleton, or the 2-positionof a triphenylene skeleton.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound which has a phenyl group bonded to anaphthalene skeleton, a phenanthrene skeleton, or a triphenyleneskeleton and which has a molecular weight greater than or equal to 350and less than or equal to 2000, and an inorganic compound exhibiting anelectron-accepting property with respect to the hydrocarbon compound. Inthe hydrocarbon compound, the phenyl group has one or more substituents,and the substituent or substituents have one or more rings selected froma benzene ring, a naphthalene ring, a phenanthrene ring, and atriphenylene ring.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound which has a molecular weight greaterthan or equal to 350 and less than or equal to 2000 and which exhibitsan absorption peak at a shorter wavelength than visible-lightwavelengths, and an inorganic compound exhibiting an electron-acceptingproperty with respect to the hydrocarbon compound. In the hydrocarboncompound, a phenyl group is bonded to a naphthalene skeleton, aphenanthrene skeleton, or a triphenylene skeleton; the phenyl group hasone or more substituents; and the substituent or substituents have oneor more rings selected from a benzene ring, a naphthalene ring, aphenanthrene ring, and a triphenylene ring.

The hydrocarbon compound in which a phenyl group with small conjugationis bonded to a naphthalene skeleton, a phenanthrene skeleton, or atriphenylene skeleton is preferred because, even when a substituent isfurther bonded to the phenyl group, the conjugation is difficult toextend and accordingly a light-transmitting property can be maintained.Further, in the composite material, use of the hydrocarbon compound ispreferred because such use can suppress the occurrence of lightabsorption due to charge-transfer interaction and can also provide thestable film quality of the composite material. Furthermore, since theconjugation becomes difficult to extend, such use is effective also interms of improving the light-transmitting property.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound which has a phenyl group bonded to theα- or β-position of a naphthalene skeleton, the 9-position of aphenanthrene skeleton, or the 2-position of a triphenylene skeleton andwhich has a molecular weight greater than or equal to 350 and less thanor equal to 2000, and an inorganic compound exhibiting anelectron-accepting property with respect to the hydrocarbon compound. Inthe hydrocarbon compound, the phenyl group has one or more substituents,and the substituent or substituents have one or more rings selected froma benzene ring, a naphthalene ring, a phenanthrene ring, and atriphenylene ring.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound which has a molecular weight greaterthan or equal to 350 and less than or equal to 2000 and which exhibitsan absorption peak at a shorter wavelength than visible-lightwavelengths, and an inorganic compound exhibiting an electron-acceptingproperty with respect to the hydrocarbon compound. In the hydrocarboncompound, a phenyl group is bonded to the α- or β-position of anaphthalene skeleton, the 9-position of a phenanthrene skeleton, or the2-position of a triphenylene skeleton; the phenyl group has one or moresubstituents; and the substituent or substituents have one or more ringsselected from a benzene ring, a naphthalene ring, a phenanthrene ring,and a triphenylene ring.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound represented by a general formula (G1)and an inorganic compound exhibiting an electron-accepting property withrespect to the hydrocarbon compound.

In the formula, R¹ to R⁹ independently represent hydrogen, an alkylgroup having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbonatoms in a ring, and R¹⁹ to R¹⁴ independently represent hydrogen, analkyl group having 1 to 6 carbon atoms, a substituted or unsubstitutedphenyl group, a substituted or unsubstituted naphthyl group, asubstituted or unsubstituted phenanthryl group, or a substituted orunsubstituted triphenylenyl group. Note that at least one of R¹⁹ to R¹⁴represents a substituted or unsubstituted phenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted phenanthrylgroup, or a substituted or unsubstituted triphenylenyl group.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound represented by a general formula (G2)and an inorganic compound exhibiting an electron-accepting property withrespect to the hydrocarbon compound.

In the formula, R²¹ to R²⁷ independently represent hydrogen, an alkylgroup having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbonatoms in a ring, and R³⁰ to R³⁴ independently represent hydrogen, analkyl group having 1 to 6 carbon atoms, a substituted or unsubstitutedphenyl group, a substituted or unsubstituted naphthyl group, asubstituted or unsubstituted phenanthryl group, or a substituted orunsubstituted triphenylenyl group. Note that at least one of R³⁰ to R³⁴represents a substituted or unsubstituted phenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted phenanthrylgroup, or a substituted or unsubstituted triphenylenyl group.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound represented by a general formula (G3)and an inorganic compound exhibiting an electron-accepting property withrespect to the hydrocarbon compound.

In the formula, R⁴¹ to R⁴⁷ independently represent hydrogen, an alkylgroup having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbonatoms in a ring, and R⁵⁰ to R⁵⁴ independently represent hydrogen, analkyl group having 1 to 6 carbon atoms, a substituted or unsubstitutedphenyl group, a substituted or unsubstituted naphthyl group, asubstituted or unsubstituted phenanthryl group, or a substituted orunsubstituted triphenylenyl group. Note that at least one of R⁵⁰ to R⁵⁴represents a substituted or unsubstituted phenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted phenanthrylgroup, or a substituted or unsubstituted triphenylenyl group.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound represented by a general formula (G4)and an inorganic compound exhibiting an electron-accepting property withrespect to the hydrocarbon compound.

In the formula, R⁶¹ to R⁷¹ independently represent hydrogen, an alkylgroup having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbonatoms in a ring, and R⁸⁰ to R⁸⁴ independently represent hydrogen, analkyl group having 1 to 6 carbon atoms, a substituted or unsubstitutedphenyl group, a substituted or unsubstituted naphthyl group, asubstituted or unsubstituted phenanthryl group, or a substituted orunsubstituted triphenylenyl group. Note that at least one of R⁸⁰ to R⁸⁴represents a substituted or unsubstituted phenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted phenanthrylgroup, or a substituted or unsubstituted triphenylenyl group.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound represented by a general formula (G5)and an inorganic compound exhibiting an electron-accepting property withrespect to the hydrocarbon compound.

In the formula, α¹ to α³ independently represent a phenylene group or abiphenylene group, and Ar¹ to Ar³ independently represent a substitutedor unsubstituted naphthyl group, a substituted or unsubstitutedphenanthryl group, or a substituted or unsubstituted triphenylenylgroup. In addition, k, n, and m independently represent 0 or 1. Notethat the naphthyl group is preferably an α-naphthyl group or aβ-naphthyl group. The phenanthryl group is preferably a 9-phenanthrylgroup. The triphenylenyl group is preferably a triphenylen-2-yl group.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound which has a substituent bonded to anaphthalene skeleton, a phenanthrene skeleton, or a triphenyleneskeleton and which has a molecular weight greater than or equal to 350and less than or equal to 2000, and a transition metal oxide. In thehydrocarbon compound, the substituent has one or more rings selectedfrom a benzene ring, a naphthalene ring, a phenanthrene ring, and atriphenylene ring.

The above-described composite material has a high carrier-transportproperty. The above-described composite material also has a goodproperty of carrier injection into an organic compound. Further, in thecomposite material, light absorption due to charge-transfer interactionis unlikely to occur. Furthermore, the composite material has a highlight-transmitting property.

The hydrocarbon compound included in the composite material of oneembodiment of the present invention, which has a substituent bonded to anaphthalene skeleton, a phenanthrene skeleton, or a triphenyleneskeleton (the substituent has one or more rings selected from a benzenering, a naphthalene ring, a phenanthrene ring, and a triphenylene ring)and which has a molecular weight greater than or equal to 350 and lessthan or equal to 2000, exhibits an absorption peak at a shorterwavelength than visible-light wavelengths (380 nm to 760 nm).

In the above composite material, the occurrence of light absorption dueto charge-transfer interaction can be suppressed and an absorption peakof the hydrocarbon compound itself can also be controlled so as toappear at a shorter wavelength than visible-light wavelengths.Accordingly, the composite material can have a high light-transmittingproperty.

A naphthalene skeleton, a phenanthrene skeleton, and a triphenyleneskeleton each have a rigid structure; therefore, the molecular weight ofthe hydrocarbon compound is preferably 350 or more because the filmquality of the composite material is stable with such a molecularweight. More preferably, the molecular weight is 450 or more. Althoughthere is no limitation on the maximum molecular weight, the molecularweight is preferably 2000 or less in consideration of evaporativity whenthe composite material is subjected to heating evaporation.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound which has a molecular weight greaterthan or equal to 350 and less than or equal to 2000 and which exhibitsan absorption peak at a shorter wavelength than visible-lightwavelengths, and a transition metal oxide. In the hydrocarbon compound,a substituent is bonded to a naphthalene skeleton, a phenanthreneskeleton, or a triphenylene skeleton, and the substituent has one ormore rings selected from a benzene ring, a naphthalene ring, aphenanthrene ring, and a triphenylene ring.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound which has a substituent bonded to theα- or β-position of a naphthalene skeleton, the 9-position of aphenanthrene skeleton, or the 2-position of a triphenylene skeleton andwhich has a molecular weight greater than or equal to 350 and less thanor equal to 2000, and a transition metal oxide. In the hydrocarboncompound, the substituent has one or more rings selected from a benzenering, a naphthalene ring, a phenanthrene ring, and a triphenylene ring.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound which has a molecular weight greaterthan or equal to 350 and less than or equal to 2000 and which exhibitsan absorption peak at a shorter wavelength than visible-lightwavelengths, and a transition metal oxide. In the hydrocarbon compound,a substituent is bonded to the α- or β-position of a naphthaleneskeleton, the 9-position of a phenanthrene skeleton, or the 2-positionof a triphenylene skeleton, and the substituent has one or more ringsselected from a benzene ring, a naphthalene ring, a phenanthrene ring,and a triphenylene ring.

In the composite material, the occurrence of light absorption due tocharge-transfer interaction can be suppressed by use of the hydrocarboncompound having a substituent at the α- or β-position of a naphthaleneskeleton, the 9-position of a phenanthrene skeleton, or the 2-positionof a triphenylene skeleton.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound which has a phenyl group bonded to anaphthalene skeleton, a phenanthrene skeleton, or a triphenyleneskeleton and which has a molecular weight greater than or equal to 350and less than or equal to 2000, and a transition metal oxide. In thehydrocarbon compound, the phenyl group has one or more substituents, andthe substituent or substituents have one or more rings selected from abenzene ring, a naphthalene ring, a phenanthrene ring, and atriphenylene ring.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound which has a molecular weight greaterthan or equal to 350 and less than or equal to 2000 and which exhibitsan absorption peak at a shorter wavelength than visible-lightwavelengths, and a transition metal oxide. In the hydrocarbon compound,a phenyl group is bonded to a naphthalene skeleton, a phenanthreneskeleton, or a triphenylene skeleton; the phenyl group has one or moresubstituents; and the substituent or substituents have one or more ringsselected from a benzene ring, a naphthalene ring, a phenanthrene ring,and a triphenylene ring.

The hydrocarbon compound in which a phenyl group with small conjugationis bonded to a naphthalene skeleton, a phenanthrene skeleton, or atriphenylene skeleton is preferred because, even when a substituent isfurther bonded to the phenyl group, the conjugation is difficult toextend and accordingly a light-transmitting property can be maintained.Further, in the composite material, use of the hydrocarbon compound ispreferred because such use can suppress the occurrence of lightabsorption due to charge-transfer interaction and can also provide thestable film quality of the composite material. Furthermore, since theconjugation becomes difficult to extend, such use is effective also interms of improving the light-transmitting property.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound which has a phenyl group bonded to theα- or β-position of a naphthalene skeleton, the 9-position of aphenanthrene skeleton, or the 2-position of a triphenylene skeleton andwhich has a molecular weight greater than or equal to 350 and less thanor equal to 2000, and a transition metal oxide. In the hydrocarboncompound, the phenyl group has one or more substituents, and thesubstituent or substituents have one or more rings selected from abenzene ring, a naphthalene ring, a phenanthrene ring, and atriphenylene ring.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound which has a molecular weight greaterthan or equal to 350 and less than or equal to 2000 and which exhibitsan absorption peak at a shorter wavelength than visible-lightwavelengths, and a transition metal oxide. In the hydrocarbon compound,a phenyl group is bonded to the α- or β-position of a naphthaleneskeleton, the 9-position of a phenanthrene skeleton, or the 2-positionof a triphenylene skeleton; the phenyl group has one or moresubstituents; and the substituent or substituents have one or more ringsselected from a benzene ring, a naphthalene ring, a phenanthrene ring,and a triphenylene ring.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound represented by the general formula (G1)and a transition metal oxide.

In the formula, R¹ to R⁹ independently represent hydrogen, an alkylgroup having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbonatoms in a ring, and R¹⁰ to R¹⁴ independently represent hydrogen, analkyl group having 1 to 6 carbon atoms, a substituted or unsubstitutedphenyl group, a substituted or unsubstituted naphthyl group, asubstituted or unsubstituted phenanthryl group, or a substituted orunsubstituted triphenylenyl group. Note that at least one of R¹⁰ to R¹⁴represents a substituted or unsubstituted phenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted phenanthrylgroup, or a substituted or unsubstituted triphenylenyl group.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound represented by the general formula (G2)and a transition metal oxide.

In the formula, R²¹ to R²⁷ independently represent hydrogen, an alkylgroup having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbonatoms in a ring, and R³⁰ to R³⁴ independently represent hydrogen, analkyl group having 1 to 6 carbon atoms, a substituted or unsubstitutedphenyl group, a substituted or unsubstituted naphthyl group, asubstituted or unsubstituted phenanthryl group, or a substituted orunsubstituted triphenylenyl group. Note that at least one of R³⁰ to R³⁴represents a substituted or unsubstituted phenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted phenanthrylgroup, or a substituted or unsubstituted triphenylenyl group.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound represented by the general formula (G3)and a transition metal oxide.

In the formula, R⁴¹ to R⁴⁷ independently represent hydrogen, an alkylgroup having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbonatoms in a ring, and R⁵⁰ to R⁵⁴ independently represent hydrogen, analkyl group having 1 to 6 carbon atoms, a substituted or unsubstitutedphenyl group, a substituted or unsubstituted naphthyl group, asubstituted or unsubstituted phenanthryl group, or a substituted orunsubstituted triphenylenyl group. Note that at least one of R⁵⁰ to R⁵⁴represents a substituted or unsubstituted phenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted phenanthrylgroup, or a substituted or unsubstituted triphenylenyl group.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound represented by the general formula (G4)and a transition metal oxide.

In the formula, R⁶¹ to R⁷¹ independently represent hydrogen, an alkylgroup having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbonatoms in a ring, and R⁸⁰ to R⁸⁴ independently represent hydrogen, analkyl group having 1 to 6 carbon atoms, a substituted or unsubstitutedphenyl group, a substituted or unsubstituted naphthyl group, asubstituted or unsubstituted phenanthryl group, or a substituted orunsubstituted triphenylenyl group. Note that at least one of R⁸⁰ to R⁸⁴represents a substituted or unsubstituted phenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted phenanthrylgroup, or a substituted or unsubstituted triphenylenyl group.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound represented by the general formula (G5)and a transition metal oxide.

In the formula, α¹ to α³ independently represent a phenylene group or abiphenylene group, and Ar¹ to Ar³ independently represent a substitutedor unsubstituted naphthyl group, a substituted or unsubstitutedphenanthryl group, or a substituted or unsubstituted triphenylenylgroup. In addition, k, n, and m independently represent 0 or 1. Notethat the naphthyl group is preferably an α-naphthyl group or aβ-naphthyl group. The phenanthryl group is preferably a 9-phenanthrylgroup. The triphenylenyl group is preferably a triphenylen-2-yl group.

The transition metal oxide included in the above-described compositematerial is preferably one or more types of oxides selected fromtitanium oxide, vanadium oxide, tantalum oxide, molybdenum oxide,tungsten oxide, rhenium oxide, ruthenium oxide, chromium oxide,zirconium oxide, hafnium oxide, and silver oxide.

Although there is no particular limitation on the highest occupiedmolecular orbital level (HOMO level) of the hydrocarbon compound used inthe above composite material, the hydrocarbon compound used in oneembodiment of the present invention has a relatively deep HOMO level(specifically, lower than or equal to −5.7 eV). Accordingly, theoccurrence of light absorption due to charge-transfer interaction can besuppressed. Therefore, the HOMO level of the hydrocarbon compound usedin the above composite material is preferably lower than or equal to−5.7 eV when measured by photoelectron spectroscopy.

Another embodiment of the present invention is a light-emitting elementincluding a layer containing a light-emitting substance (hereinafteralso referred to as EL layer) between a pair of electrodes. The layercontaining a light-emitting substance includes a layer containing theabove-described composite material.

In the above-described light-emitting element, it is preferable that thelayer containing the composite material be in contact with one of thepair of electrodes which functions as an anode. It is also preferablethat the layer containing the composite material be in contact with oneof the pair of electrodes which functions as a cathode.

The above-described light-emitting element may include two layerscontaining the composite material, and it is preferable that one of thetwo layers containing the composite material be in contact with one ofthe pair of electrodes which functions as an anode and the other of thetwo layers be in contact with the other of the pair of electrodes whichfunctions as a cathode.

As described above, the hydrocarbon compound used in one embodiment ofthe present invention has a relatively deep HOMO level (specifically,lower than or equal to −5.7 eV). Accordingly, even when an organiccompound used in a layer, which is in contact with a surface of thelayer containing the above composite material and closer than thesurface to the cathode, (an organic compound used in a hole-transportlayer, a light-emitting layer, or the like) has a relatively deep HOMOlevel (e.g., −6.0 eV), hole injection from the above composite materialinto the organic compound can be efficient. Needless to say, even whenthe organic compound has a shallow HOMO level (e.g., −5.0 eV), holeinjection from the above composite material into the organic compoundcan be efficient. Therefore, the HOMO level of the organic compoundcontained in the layer (hereinafter, referred to as first layer), whichis in contact with a surface of the layer containing the above compositematerial and closer than the surface to the cathode, is preferablyhigher than or equal to −6.0 eV and lower than or equal to −5.0 eV.

A HOMO level difference between the above composite material and theorganic compound is preferably small and preferably within 0.2 eV. Onthe basis of the view that the HOMO level difference between the organiccompound used in the first layer and the hydrocarbon compound used inthe above composite material is made small as described above, ahydrocarbon compound which has a substituent bonded to a naphthaleneskeleton, a phenanthrene skeleton, or a triphenylene skeleton (thesubstituent has one or more rings selected from a benzene ring, anaphthalene ring, a phenanthrene ring, and a triphenylene ring) andwhich has a molecular weight greater than or equal to 350 and less thanor equal to 2000, like the hydrocarbon compound used in the abovecomposite material, is preferably used as the organic compound used inthe first layer. For example, the same hydrocarbon compound as that usedin the above composite material can be used.

From the same view, a light-emitting layer in contact with the firstlayer also preferably contains (especially, as a host material) ahydrocarbon compound which has a substituent bonded to a naphthaleneskeleton, a phenanthrene skeleton, or a triphenylene skeleton (thesubstituent has one or more rings selected from a benzene ring, anaphthalene ring, a phenanthrene ring, and a triphenylene ring) andwhich has a molecular weight greater than or equal to 350 and less thanor equal to 2000, like the hydrocarbon compound used in the abovecomposite material. For example, the same hydrocarbon compound as thatused in the above composite material can be used.

In other words, one embodiment of the present invention is alight-emitting element including a layer containing a light-emittingsubstance between a pair of electrodes. The layer containing alight-emitting substance includes, on its anode side, a layer containingthe above composite material, the first layer, and the light-emittinglayer. The layer containing the above composite material, the firstlayer, and the light-emitting layer each contain a hydrocarbon compoundwhich has a substituent bonded to a naphthalene skeleton, a phenanthreneskeleton, or a triphenylene skeleton (the substituent has one or morerings selected from a benzene ring, a naphthalene ring, a phenanthrenering, and a triphenylene ring) and which has a molecular weight greaterthan or equal to 350 and less than or equal to 2000.

The hydrocarbon compounds contained in each of the layer containing thecomposite material, the first layer, and the light-emitting layer arepreferably the same because, in such a case, hole injection throughthese layers are efficient and synthesis costs can be cut down.

Another embodiment of the present invention is a light-emitting elementwhich includes a plurality of EL layers between a pair of electrodes,and which includes a layer containing the above-described compositematerial between the plurality of EL layers. In other words, theabove-described composite material can be used for an intermediate layer(also referred to as charge-generation layer) in an organic ELlight-emitting element including a stack of a plurality oflight-emitting units (a tandem organic EL light-emitting element). Inthis structure, it is preferable to provide a layer containing ahydrocarbon compound which has a substituent bonded to a naphthaleneskeleton, a phenanthrene skeleton, or a triphenylene skeleton (thesubstituent has one or more rings selected from a benzene ring, anaphthalene ring, a phenanthrene ring, and a triphenylene ring) andwhich has a molecular weight greater than or equal to 350 and less thanor equal to 2000, so as to be in contact with a surface of the layercontaining the composite material and closer than the surface to thecathode.

Another embodiment of the present invention is a light-emitting deviceincluding the above-described light-emitting element. Another embodimentof the present invention is an electronic device including thelight-emitting device in a display portion. Another embodiment of thepresent invention is a lighting device including the light-emittingelement in a light-emitting portion.

Of one embodiment of the present invention, it is possible to provide acomposite material which includes an organic compound and an inorganiccompound and which has a high carrier-transport property. It is alsopossible to provide a composite material having a good property ofcarrier injection into an organic compound. It is also possible toprovide a composite material in which light absorption due tocharge-transfer interaction is unlikely to occur. It is also possible toprovide a composite material having a high visible-light-transmittingproperty.

Of one embodiment of the present invention, it is possible to provide alight-emitting element having high emission efficiency by applying theabove-described composite material to the light-emitting element. It isalso possible to provide a light-emitting element having a low drivingvoltage. It is also possible to provide a light-emitting element havinga long lifetime. It is possible to provide a light-emitting deviceincluding the light-emitting element, an electronic device including thelight-emitting device, or a lighting device including the light-emittingdevice.

BRIEF DESCRIPTION OF THE DRAWINGS

In the accompanying drawings:

FIGS. 1A to 1C each illustrate a light-emitting element of oneembodiment of the present invention;

FIGS. 2A and 2B each illustrate a light-emitting element of oneembodiment of the present invention;

FIGS. 3A and 3B illustrate a light-emitting device of one embodiment ofthe present invention;

FIGS. 4A and 4B illustrate a light-emitting device of one embodiment ofthe present invention;

FIGS. 5A to 5E each illustrate an electronic device of one embodiment ofthe present invention;

FIG. 6 illustrates a lighting device of one embodiment of the presentinvention;

FIGS. 7A and 7B show absorbances of N3P and a composite material thereofaccording to Example 1;

FIGS. 8A and 8B show absorbances of Pn3P and a composite materialthereof according to Example 1;

FIGS. 9A and 9B show absorbances of P4N and a composite material thereofaccording to Example 1;

FIGS. 10A and 10B show absorbances of DPAnth and a composite materialthereof according to Example 1;

FIG. 11 shows luminance versus voltage characteristics of alight-emitting element of Example 2;

FIG. 12 shows current efficiency versus luminance characteristics of thelight-emitting element of Example 2;

FIG. 13 shows results of a reliability test of the light-emittingelement of Example 2;

FIG. 14 shows luminance versus voltage characteristics of alight-emitting element of Example 3;

FIG. 15 shows current efficiency versus luminance characteristics of thelight-emitting element of Example 3;

FIG. 16 shows results of a reliability test of the light-emittingelement of Example 3;

FIG. 17 shows luminance versus voltage characteristics of alight-emitting element of Example 4;

FIG. 18 shows current efficiency versus luminance characteristics of thelight-emitting element of Example 4;

FIG. 19 shows results of a reliability test of the light-emittingelement of Example 4;

FIG. 20 shows luminance versus voltage characteristics of alight-emitting element of Example 5;

FIG. 21 shows current efficiency versus luminance characteristics of thelight-emitting element of Example 5;

FIG. 22 shows results of a reliability test of the light-emittingelement of Example 5;

FIG. 23 shows luminance versus voltage characteristics of light-emittingelements of Example 6;

FIG. 24 shows current efficiency versus luminance characteristics of thelight-emitting elements of Example 6;

FIG. 25 shows results of reliability tests of the light-emittingelements of Example 5;

FIGS. 26A and 26B each illustrate a light-emitting element in Examples;

FIGS. 27A to 27C illustrate light-emitting devices of embodiments of thepresent invention;

FIG. 28 shows current efficiency versus luminance characteristics of alight-emitting element of Example 7;

FIG. 29 shows current versus voltage characteristics of thelight-emitting element of Example 7;

FIG. 30 shows chromaticity coordinate versus luminance characteristicsof the light-emitting element of Example 7;

FIG. 31 shows an emission spectrum of the light-emitting element ofExample 7;

FIGS. 32A and 32B show an absorption and emission spectra of N3P in atoluene solution of N3P;

FIGS. 33A and 33B show an absorption and emission spectra of Pn3P in atoluene solution of Pn3P;

FIGS. 34A and 34B show an absorption and emission spectra of βN3P in atoluene solution of βN3P;

FIGS. 35A and 35B show absorbances of βN3P and a composite materialthereof according to Example 8;

FIG. 36 shows luminance versus voltage characteristics of alight-emitting element of Example 9.

FIG. 37 shows current efficiency versus luminance characteristics of thelight-emitting element of Example 9.

FIG. 38 shows luminance versus voltage characteristics of alight-emitting element of Example 10;

FIG. 39 shows current efficiency versus luminance characteristics of thelight-emitting element of Example 10;

FIG. 40 shows results of a reliability test of the light-emittingelement of Example 10; and

FIGS. 41A and 41B show an absorption and emission spectra of mPnBP in atoluene solution of mPnBP.

DETAILED DESCRIPTION OF THE INVENTION

Embodiments will be described in detail with reference to the drawings.Note that the present invention is not limited to the followingdescription and it will be readily appreciated by those skilled in theart that the modes and details of the present invention can be modifiedin various ways without departing from the spirit and scope thereof.Therefore, the present invention should not be interpreted as beinglimited to the description in the following embodiments and examples.Note that the same portions or portions having similar functions arecommonly denoted by the same reference numerals in different drawings,and repetitive description thereof is omitted.

First, a difference between the background art of the present inventionand the present invention will be briefly described. As disclosed inPatent Document 1, it is interpreted that in a composite materialincluding a mixture of an aromatic amine and an electron-acceptinginorganic compound, the electron-accepting inorganic compound takeselectrons from the aromatic amine, and accordingly, holes and electronsare generated in the aromatic amine and the inorganic compound,respectively. In other words, it is interpreted that in such a compositematerial, the aromatic amine and the electron-accepting inorganiccompound form a charge-transfer complex. Some composite materialsutilizing such a phenomenon and having excellent carrier-transportand/or carrier-injection properties have been reported so far.

However, it is generally known that an absorption band based oncharge-transfer interaction is generated in such composite materials.This absorption band is said to be generated in the deep-red tonear-infrared regions; actually, in many cases, an absorption band isalso generated in the visible light region. For example, a compositematerial including a mixture of4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB orα-NPB) and vanadium oxide or a mixture of NPB and molybdenum oxide hasan absorption band at around 500 nm, in addition to an absorption bandat around 1300 nm. This is a great disadvantage for optical devices suchas light-emitting elements.

The present inventors have found that, despite the fact that no lightabsorption due to charge-transfer interaction can be observed (lightabsorption hardly occurs), excellent carrier-transport and/orcarrier-injection properties can be exhibited by a composite material ofan inorganic compound exhibiting an electron-accepting property and ahydrocarbon compound which has a substituent bonded to a naphthaleneskeleton, a phenanthrene skeleton, or a triphenylene skeleton (thesubstituent has one or more rings selected from a benzene ring, anaphthalene ring, a phenanthrene ring, and a triphenylene ring) andwhich has a molecular weight greater than or equal to 350 and less thanor equal to 2000 or by a composite material of a transition metal oxideand the hydrocarbon compound. It has been considered that holes andelectrons generated due to charge-transfer interaction are factors forexhibiting carrier-transport and/or carrier-injection properties.Therefore, it can be said that the present invention, which can provideexcellent carrier-transport and/or carrier-injection properties despitethe fact that no clear light absorption due to charge-transferinteraction is observed, contradicts the general theory and provides aremarkable and unexpected function.

As described above, the hydrocarbon compound used in one embodiment ofthe present invention has a naphthalene skeleton, a phenanthreneskeleton, or a triphenylene skeleton. In addition, the one or moresubstituents bonded to the skeleton have one or more rings selected froma benzene ring, a naphthalene ring, a phenanthrene ring, and atriphenylene ring. Benzene, naphthalene, phenanthrene, and triphenyleneeach have a large energy gap of its own. Therefore, when the ringselected from the above is used for the hydrocarbon compound, thehydrocarbon compound can be designed so as not to have an absorptionpeak in the visible light region (so as to have little absorption in thevisible light region). Accordingly, there is a great advantage in termsof improving the light-transmitting property.

Further, cyclic voltammetry (CV) shows that the HOMO levels ofnaphthalene, phenanthrene, and triphenylene are very low. Therefore, itcan be considered that the hydrocarbon compound, which is used in oneembodiment of the present invention, by itself is excellent in holeinjection into another organic compound, but has difficulty receivingholes from an electrically conductive material typified by Al or ITO(having a work function of approximately 3 eV to 5 eV). However,formation of such a composite material as in one embodiment of thepresent invention enables the problem in hole injection from anelectrode to be overcome while maintaining an excellent property of holeinjection into another organic compound. When the composite material isused for a light-emitting element, such a property of the compositematerial contributes to a reduction in driving voltage. Further, thehigh light-transmitting property leads to an increase in emissionefficiency. Furthermore, the deep HOMO level is considered to preventcarrier accumulation in a light-emitting element carrier accumulation ina light-emitting element, leasing to a longer lifetime.

Embodiments of the present invention will be described below withspecific examples.

Embodiment 1

In this embodiment, a composite material of one embodiment of thepresent invention is described.

The composite material of one embodiment of the present invention is acomposite material of an organic compound having a particular skeletonand an inorganic compound. There is no limitation on a method ofpreparing the composite material of one embodiment of the presentinvention; for example, it can be formed by a co-evaporation method inwhich the organic compound and the inorganic compound are deposited atthe same time. The mixing ratio of the organic compound to the inorganiccompound in the composite material of one embodiment of the presentinvention is preferably approximately 8:1 to 1:2 (=organiccompound:inorganic compound) and more desirably 4:1 to 1:1 (=organiccompound:inorganic compound) in mass ratio. When the composite materialis formed by a co-evaporation method, the mixing ratio can be controlledby separately adjusting the deposition rates for the organic compoundand the inorganic compound.

First, an organic compound that can be used for the composite materialof one embodiment of the present invention is a hydrocarbon compoundwhich has a substituent bonded to a naphthalene skeleton, a phenanthreneskeleton, or a triphenylene skeleton and which has a molecular weightgreater than or equal to 350 and less than or equal to 2000. Note thatthe substituent has one or more rings selected from a benzene ring, anaphthalene ring, a phenanthrene ring, and a triphenylene ring.

The composite material including the hydrocarbon compound has a highcarrier-transport property. The composite material also has a goodproperty of carrier injection into an organic compound. Further, in thecomposite material, light absorption due to charge-transfer interactionwith an inorganic compound is unlikely to occur. Furthermore, thecomposite material has a high light-transmitting property.

In the composite material including the hydrocarbon compound, theoccurrence of light absorption due to charge-transfer interaction can besuppressed and an absorption peak of the hydrocarbon compound itself canalso be controlled so as to appear at a shorter wavelength thanvisible-light wavelengths. Accordingly, the composite material can havea high light-transmitting property.

Naphthalene, phenanthrene, and triphenylene are condensed rings, and aretherefore important conjugated rings for exhibiting a carrier-transportproperty (especially a hole-transport property). Further, the ring ofthe above substituent (one or more rings selected from a benzene ring, anaphthalene ring, a phenanthrene ring, and a triphenylene ring) is animportant conjugated ring for enhancing a carrier-transport property(especially a hole-transport property), and is at the same time aconjugated ring having a wide energy gap. Accordingly, when the ring ofthe above substituent is limited to these rings, the occurrence of lightabsorption due to charge-transfer interaction can be suppressed and anabsorption peak of the hydrocarbon compound itself can also becontrolled so as to appear; thus, with the use of the hydrocarboncompound, the composite material can have a high light-transmittingproperty.

Although there is no particular limitation on a method of preparing thecomposite material, co-evaporation of the hydrocarbon compound and aninorganic compound is preferred, in which case the hydrocarbon compoundis expected to vaporize readily. Therefore, in terms of molecularweight, the molecular weight of the hydrocarbon compound is preferablyless than or equal to 2000. When an alkyl chain or the like is bonded tothe hydrocarbon compound and the composite material is prepared througha wet process (a method in which a solution is used to form a film) orthe like, the molecular weight may be greater than or equal to 2000.

The results of experiments and studies conducted by the presentinventors have shown that a composite material formed by combining anaromatic hydrocarbon compound (e.g., an anthracene compound) and aninorganic compound can be easily crystallized when the mixing ratio ofthe inorganic compound to the aromatic compound is low (see the resultsin Comparison Example in Example 1 described later). In contrast, whenthe mixing ratio of the inorganic compound is high, although suchcrystallization can be suppressed, slight absorption peaks, which resultfrom charge-transfer interaction between a skeleton of the aromatichydrocarbon compound (e.g., an anthracene skeleton) and the inorganiccompound increase in the visible light region. On the other hand, in thecase where a hydrocarbon compound having a substituent bonded to anaphthalene skeleton, a phenanthrene skeleton, or a triphenyleneskeleton (the substituent has one or more rings selected from a benzenering, a naphthalene ring, a phenanthrene ring, and a triphenylene ring)is used as illustrated in one embodiment of the present invention,crystallization of the composite material is suppressed and the filmquality thereof is stable. Therefore, in the case of the compositematerial of one embodiment of the present invention, it is not necessaryto increase the proportion of the inorganic compound for the purpose ofsuppressing the crystallization, and it is possible to prevent anabsorption peak resulting from charge-transfer interaction from beingobserved in the visible light region.

It is especially preferable to use a hydrocarbon compound having asubstituent bonded to the α- or β-position of a naphthalene skeleton,the 9-position of a phenanthrene skeleton, or the 2-position of atriphenylene skeleton. Note that the substituent has one or more ringsselected from a benzene ring, a naphthalene ring, a phenanthrene ring,and a triphenylene ring. In the composite material, use of such ahydrocarbon compound can suppress the occurrence of light absorption dueto charge-transfer interaction.

With a bulky substituent (having 6 or more carbon atoms, for example) atthe α- or β-position of a naphthalene skeleton, the 9-position of aphenanthrene skeleton, or the 2-position of a triphenylene skeleton, themolecule as a whole is a steric structure due to steric hindrancebetween the skeleton and the substituent. Consequently, the film qualityof the composite material is stable.

It is preferable that a phenyl group be bonded to a naphthaleneskeleton, a phenanthrene skeleton, or a triphenylene skeleton and thephenyl group have one or more substituents. Note that the substituenthas one or more rings selected from a benzene ring, a naphthalene ring,a phenanthrene ring, and a triphenylene ring.

Since the phenyl group has small conjugation, even when the molecularweight is increased by bonding an additional substituent to the phenylgroup, the hydrocarbon compound can maintain a wide energy gap, which isalso effective in terms of improving a light-transmitting property.Further, in the composite material, use of the hydrocarbon compound ispreferred because such use can suppress the occurrence of lightabsorption due to charge-transfer interaction.

Furthermore, with a bulky site (for example, a skeleton having a totalof 12 or more carbon atoms including the above phenyl group) at the α-or β-position of a naphthalene skeleton, the 9-position of aphenanthrene skeleton, or the 2-position of a triphenylene skeleton, themolecule as a whole is a steric structure due to steric hindrancebetween the bulky site and the naphthalene skeleton, phenanthreneskeleton, or triphenylene skeleton. Consequently, the film quality ofthe composite material is stable.

To make the structure of the hydrocarbon compound bulkier, it ispreferable that the hydrocarbon compound used for the above compositematerial be a compound to which three or more hydrocarbon skeletons arebonded, and particularly preferable that two of the hydrocarbonskeletons be any of a naphthalene skeleton, a phenanthrene skeleton, anda triphenylene skeleton.

When the composite material is prepared, co-evaporation of thehydrocarbon compound and an inorganic compound is preferred, in whichcase the hydrocarbon compound is expected to vaporize readily. Thus, themolecular weight of the hydrocarbon compound is preferably approximatelyless than or equal to 2000.

Naphthalene, phenanthrene, and triphenylene are condensed rings, and aretherefore important conjugated rings for exhibiting a carrier-transportproperty (especially a hole-transport property). Further, the ring ofthe above substituent (one or more rings selected from a benzene ring, anaphthalene ring, a phenanthrene ring, and a triphenylene ring) is animportant conjugated ring for enhancing a carrier-transport property(especially a hole-transport property), and is at the same time aconjugated ring having a wide energy gap. Accordingly, when the ring ofthe above substituent is limited to these rings, the occurrence of lightabsorption due to charge-transfer interaction can be suppressed and anabsorption peak of the hydrocarbon compound itself can also becontrolled so as to appear; thus, with the use of the hydrocarboncompound, the composite material can have a high light-transmittingproperty.

The phenyl group preferably has the substituent at the meta-position, inwhich case the band gap of the hydrocarbon compound can be kept wide,and a more steric structure can be formed to make crystallization moredifficult. The phenyl group preferably has the substituent at thepara-position, in which case the carrier-transport property of thehydrocarbon compound is excellent.

In one embodiment of the present invention, by including a phenanthreneskeleton, the hydrocarbon compound can be designed so as to have a highmolecular weight while maintaining a high light-transmitting property.The hydrocarbon compound has good thermophysical properties and istherefore preferred. In addition, by use of the composite materialincluding the hydrocarbon compound, a light-emitting element having alow driving voltage can be obtained.

One embodiment of the present invention is therefore a compositematerial including a hydrocarbon compound represented by the generalformula (G1) and an inorganic compound exhibiting an electron-acceptingproperty with respect to the hydrocarbon compound.

In the formula, R¹ to R⁹ independently represent hydrogen, an alkylgroup having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbonatoms in a ring, R¹⁰ to R¹⁴ independently represent hydrogen, an alkylgroup having 1 to 6 carbon atoms, a substituted or unsubstituted phenylgroup, a substituted or unsubstituted naphthyl group, a substituted orunsubstituted phenanthryl group, or a substituted or unsubstitutedtriphenylenyl group. Note that at least one of R¹⁰ to R¹⁴ represents asubstituted or unsubstituted phenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted phenanthrylgroup, or a substituted or unsubstituted triphenylenyl group.

In one embodiment of the present invention, the hydrocarbon compound canbe designed so as to have a wide energy gap by including a naphthaleneskeleton. The hydrocarbon compound does not exhibit an absorption peakin the visible light region and is therefore preferred. In addition, byuse of the composite material including the hydrocarbon compound, alight-emitting element having high emission efficiency can be obtained.

One embodiment of the present invention is therefore a compositematerial including a hydrocarbon compound represented by the generalformula (G2) and an inorganic compound exhibiting an electron-acceptingproperty with respect to the hydrocarbon compound.

In the formula, R²¹ to R²⁷ independently represent hydrogen, an alkylgroup having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbonatoms in a ring, and R³⁰ to R³⁴ independently represent hydrogen, analkyl group having 1 to 6 carbon atoms, a substituted or unsubstitutedphenyl group, a substituted or unsubstituted naphthyl group, asubstituted or unsubstituted phenanthryl group, or a substituted orunsubstituted triphenylenyl group. Note that at least one of R³⁰ to R³⁴represents a substituted or unsubstituted phenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted phenanthrylgroup, or a substituted or unsubstituted triphenylenyl group.

The β-position is preferable to the α-position as the position of anaphthalene skeleton at which the phenyl group is bonded because, in thecase of the β-position, steric hindrance with another substituent can bereduced and accordingly synthesis can be facilitated. The α-position ispreferable because, in the case of the α-position, the molecularstructure becomes steric and intermolecular interaction is reduced andaccordingly crystallization is made difficult, and also because rotationof the substituent (naphthyl group) in the molecule is suppressed andaccordingly the thermophysical properties (glass transition temperature)can be improved.

One embodiment of the present invention is therefore a compositematerial including a hydrocarbon compound represented by the generalformula (G3) and an inorganic compound exhibiting an electron-acceptingproperty with respect to the hydrocarbon compound.

In the formula, R⁴¹ to R⁴⁷ independently represent hydrogen, an alkylgroup having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbonatoms in a ring, and R⁵⁰ to R⁵⁴ independently represent hydrogen, analkyl group having 1 to 6 carbon atoms, a substituted or unsubstitutedphenyl group, a substituted or unsubstituted naphthyl group, asubstituted or unsubstituted phenanthryl group, or a substituted orunsubstituted triphenylenyl group. Note that at least one of R⁵⁰ to R⁵⁴represents a substituted or unsubstituted phenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted phenanthrylgroup, or a substituted or unsubstituted triphenylenyl group.

In one embodiment of the present invention, by including a triphenyleneskeleton, the hydrocarbon compound can be designed so as to have a highmolecular weight while maintaining a high light-transmitting property.The hydrocarbon compound has good thermophysical properties and istherefore preferred. The hydrocarbon compound is preferable because itmakes the molecular structure steric and reduces intermolecularinteraction and accordingly crystallization is made difficult.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound represented by the general formula (G4)and an inorganic compound exhibiting an electron-accepting property withrespect to the hydrocarbon compound.

In the formula, R⁶¹ to R⁷¹ independently represent hydrogen, an alkylgroup having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbonatoms in a ring, and R⁸⁰ to R⁸⁴ independently represent hydrogen, analkyl group having 1 to 6 carbon atoms, a substituted or unsubstitutedphenyl group, a substituted or unsubstituted naphthyl group, asubstituted or unsubstituted phenanthryl group, or a substituted orunsubstituted triphenylenyl group. Note that at least one of R⁸⁰ to R⁸⁴represents a substituted or unsubstituted phenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted phenanthrylgroup, or a substituted or unsubstituted triphenylenyl group.

Another embodiment of the present invention is a composite materialincluding a hydrocarbon compound represented by the general formula (G5)and an inorganic compound exhibiting an electron-accepting property withrespect to the hydrocarbon compound.

In the formula, α¹ to α³ independently represent a phenylene group or abiphenylene group, and Ar¹ to Ar³ independently represent a substitutedor unsubstituted naphthyl group, a substituted or unsubstitutedphenanthryl group, or a substituted or unsubstituted triphenylenylgroup. In addition, k, n, and m independently represent 0 or 1.

When the naphthyl group, phenanthryl group, or triphenylenyl group inAr¹ to Ar³ has a substituent or substituents, the substituent orsubstituents are separately an alkyl group having 1 to 6 carbon atoms ora substituted or unsubstituted phenyl group.

Examples of preferred structures of α¹ to α³ include substituentsrepresented by a general formula (α-1) to a general formula (α-5).

In the case where α¹ to α³ are independently represented by the generalformula (α-1) or the general formula (α-3) (i.e., the case where, in thegeneral formula (G5), Ar¹ to Ar³ are separately bonded to the centralbenzene ring at the para-position through a phenylene group or abiphenylene group), the hydrocarbon compound has an excellentcarrier-transport property; thus, this case is preferable. In the casewhere α¹ to α³ are independently represented by the general formula(α-2), the general formula (α-4), or the general formula (α-5) (i.e.,the case where Ar¹ to Ar³ are each bonded to the central benzene ring atthe meta-position through a phenylene group or a biphenylene group), themolecular structure of the hydrocarbon compound is steric andcrystallization is difficult; thus, this case is preferable. In the casewhere α¹ to α³ are biphenylene groups as in the general formulae (α-3)to (α-5), the thermophysical properties of the hydrocarbon compound areimproved; thus, this case is preferable.

For simplification of synthesis, all of α¹ to α³ are preferablyphenylene groups or biphenylene groups. At the same time, all of Ar¹ toAr³ are preferably substituted or unsubstituted naphthyl groups,substituted or unsubstituted phenanthryl groups, or substituted orunsubstituted triphenylenyl groups. In addition, k, n, and m arepreferably the same number and especially preferably 0. More preferably,all of Ar¹ to Ar³ are unsubstituted naphthyl groups, unsubstitutedphenanthryl groups, or unsubstituted triphenylenyl groups and k, n, andm are each 0. In this case, the step in which the same threesubstituents are bonded to benzene at once is sufficient for synthesis,and consequently, a hydrocarbon compound having a high molecular weightcan be obtained simply and inexpensively. In addition, rigidsubstituents are bonded to benzene in the propeller form to form asteric structure, so that a hydrocarbon compound having goodthermophysical properties can be obtained.

Examples of the organic compound that can be used for the compositematerial of one embodiment of the present invention are represented bythe following structural formulae (100) to (127) and (130) to (145).

Next, the inorganic compound that can be used for the composite materialof one embodiment of the present invention is described.

It is possible to use an inorganic compound exhibiting anelectron-accepting property with respect to the hydrocarbon compoundused for the composite material of one embodiment of the presentinvention. Iron(III) chloride, aluminum chloride, and the like areexamples of inorganic compounds having a high electron-acceptingproperty.

Alternatively, a transition metal oxide can be used as the inorganiccompound for the composite material of one embodiment of the presentinvention. It is preferable to use an oxide of a metal belonging to anyof Groups 4 to 8 of the periodic table. It is particularly preferable touse titanium oxide, vanadium oxide, tantalum oxide, molybdenum oxide,tungsten oxide, rhenium oxide, ruthenium oxide, chromium oxide,zirconium oxide, hafnium oxide, or silver oxide. Molybdenum oxide isparticularly easy to handle among them, because it is easily depositedby evaporation, has a low hygroscopic property, and is stable.

A transition metal oxide is considered not to have a very highelectron-accepting property (considered to have low reactivity), ascompared to a strong Lewis acid such as iron(III) chloride mentionedabove. In the composite material of one embodiment of the presentinvention, as described above, absorption due to charge-transferinteraction less occurs (or light absorption hardly occurs). It isdifficult to prove from these that a transition metal oxide acts as anelectron acceptor in a general sense in the present invention. On theother hand, as described in the following examples, there is anexperimental fact that the composite material of one embodiment of thepresent invention conducts a larger amount of current than thehydrocarbon compound alone can do, when an electric field is applied.Thus, it is probable that in the composite material of one embodiment ofthe present invention, use of a transition metal oxide facilitatescarrier generation at least with an assistance of application of anelectric field. Therefore, in this specification, an inorganic compound(such as a transition metal oxide mentioned above) in the compositematerial is considered to have an electron-accepting property as long ascarriers are generated at least with an assistance of application of anelectric field.

It is preferable that the HOMO level of the hydrocarbon compoundincluded in the above-described composite material of one embodiment ofthe present invention is lower than or equal to −5.7 eV when measured byphotoelectron spectroscopy. As described above, naphthalene,phenanthrene, and triphenylene have very low HOMO levels. Therefore, thehydrocarbon compound including a naphthalene skeleton, a phenanthreneskeleton, or a triphenylene skeleton, which is used in one embodiment ofthe present invention, can by itself have a HOMO level as low as orlower than −5.7 eV with ease.

In the case where the hydrocarbon compound has a low HOMO level, it canbe considered that the hydrocarbon compound is excellent in holeinjection into another organic compound, but has difficulty receivingholes from an electrically conductive material typified by Al or ITO(having a work function of approximately 3 eV to 5 eV). However,formation of such a composite material as in one embodiment of thepresent invention enables the problem in hole injection from anelectrode to be overcome while maintaining an excellent property of holeinjection into another organic compound. When the composite material isused for a light-emitting element, such a property of the compositematerial contributes to a reduction in driving voltage. Further, thehigh light-transmitting property leads to an increase in emissionefficiency. Furthermore, the deep HOMO level is considered to preventcarrier accumulation in a light-emitting element, leasing to a longerlifetime.

As described above, the composite material of one embodiment of thepresent invention is a material having a low HOMO level and a highcarrier-transport property. In addition, the composite material of oneembodiment of the present invention is a material having an excellentproperty of carrier injection into an organic compound. Further, thecomposite material of one embodiment of the present invention is amaterial in which absorption due to charge-transfer interaction isunlikely to occur. Furthermore, the composite material of one embodimentof the present invention is a material having a high light-transmittingproperty.

Therefore, the composite material of one embodiment of the presentinvention can be used for a light-emitting element or a semiconductorelement such as a photoelectric conversion element or a transistor.

Furthermore, the composite material of one embodiment of the presentinvention has excellent properties of carrier-transport and carrierinjection into an organic compound and can accordingly realize a lowdriving voltage when used for a light-emitting element or the like.

The composite material of one embodiment of the present invention has alight-transmitting property and can accordingly realize high emissionefficiency when used for a light-emitting element or the like.

The composite material of one embodiment of the present inventionsuppresses charge accumulation and can accordingly realize an elementhaving a long lifetime when used for a light-emitting element or thelike.

Note that this embodiment can be implemented in appropriate combinationwith any of the other embodiments.

Embodiment 2

In this embodiment, a light-emitting element of one embodiment of thepresent invention is described with reference to FIGS. 1A to 1C.

In a light-emitting element of this embodiment, an EL layer (a layercontaining a light-emitting substance) is interposed between a pair ofelectrodes. The EL layer includes at least a layer containing thecomposite material of one embodiment of the present invention describedin Embodiment 1 and a light-emitting layer. The EL layer mayadditionally include another layer. For example, the EL layer mayinclude a layer containing a substance having a high carrier-injectionproperty or a layer containing a substance having a highcarrier-transport property so that a light-emitting region is formed ina region away from the electrodes, that is, so that carriers recombinein a region away from the electrodes. In this specification, the layercontaining a substance having a high carrier-injection or a highcarrier-transport property is also referred to as functional layer whichfunctions, for instance, to inject or transport carriers. As afunctional layer, a hole-injection layer, a hole-transport layer, anelectron-injection layer, an electron-transport layer, or the like canbe used. Note that in this embodiment, the layer containing thecomposite material of one embodiment of the present invention is used asa hole-injection layer.

It is preferable that one or more layers (such as a hole-transportlayer) be provided between the layer containing the composite materialof one embodiment of the present invention and the light-emitting layer.Accordingly, it is possible to suppress quenching (an efficiencydecrease) caused by transfer of excitation energy generated in thelight-emitting layer to the layer containing the composite material, andit is possible to obtain a more efficient element.

In the light-emitting element illustrated in FIG. 1A, an EL layer 102 isprovided between a first electrode 101 and a second electrode 108. Inthe EL layer 102, a hole-injection layer 701, a hole-transport layer702, a light-emitting layer 703, an electron-transport layer 704, and anelectron-injection layer 705 are stacked in this order over the firstelectrode 101. Note that, in the light-emitting element described inthis embodiment, the first electrode 101 functions as an anode and thesecond electrode 108 functions as a cathode.

As a support of the light-emitting element (see a substrate 100 in FIG.1A), a glass substrate, a quartz substrate, a plastic substrate, or thelike can be used, for example. Furthermore, a flexible substrate may beused. The flexible substrate is a substrate that can be bent, such as aplastic substrate made of polycarbonate, polyarylate, or polyethersulfone, for example. A film (made of polypropylene, polyester, vinyl,polyvinyl fluoride, vinyl chloride, or the like), an inorganic filmformed by evaporation, or the like can also be used. Note that materialsother than these can be used as long as they can function as a supportof the light-emitting element.

For the first electrode 101, any of a variety of metals, alloys,electrically conductive compounds, mixtures thereof, and the like can beused. Examples include indium oxide-tin oxide (ITO: indium tin oxide),indium oxide-tin oxide containing silicon or silicon oxide, indiumoxide-zinc oxide (IZO: indium zinc oxide), indium oxide containingtungsten oxide and zinc oxide (IWZO), and the like. Films of theseconductive metal oxides are usually formed by sputtering, but may beformed by application of a sol-gel method or the like. For example, afilm of indium oxide-zinc oxide can be formed by a sputtering methodusing a target obtained by adding 1 wt % to 20 wt % of zinc oxide toindium oxide. Further, an IWZO film can be formed by a sputtering methodusing a target obtained by adding 0.5 wt % to 5 wt % of tungsten oxideand 0.1 wt % to 1 wt % of zinc oxide to indium oxide. Other examples aregold, platinum, nickel, tungsten, chromium, molybdenum, iron, cobalt,copper, palladium, nitrides of metal materials (e.g., titanium nitride),and the like.

As a material of the first electrode 101, it is preferable to use amaterial having a high work function (a work function higher than orequal to 4.0 eV). Note that in a light-emitting element having astructure where the first electrode 101 and the layer containing thecomposite material of one embodiment of the present invention are incontact with each other, a material used for the first electrode 101 isnot limited to a material having a high work function and can be amaterial having a low work function. For example, aluminum, silver, analloy including aluminum (e.g., Al—Si), or the like can also be used.

The hole-injection layer 701 is a layer that contains the compositematerial of one embodiment of the present invention.

The hydrocarbon compound (see Embodiment 1) used for the compositematerial of one embodiment of the present invention has a low HOMO leveland an excellent property of hole injection into the hole-transportlayer 702 and the light-emitting layer 703. On the other hand, aninjection barrier is generated between the first electrode 101 and thehydrocarbon compound, and holes are not easily injected from the firstelectrode 101.

However, in the light-emitting element of one embodiment of the presentinvention, the composite material of one embodiment of the presentinvention is used for the hole-injection layer 701; thus, the injectionbarrier between the first electrode 101 and the hole-injection layer 701can be reduced. Therefore, it is possible to realize an element having alow injection barrier from the first electrode 101 to the light-emittinglayer 703 and a high carrier-injection property, and it is possible toprovide a light-emitting element having a low driving voltage.

Furthermore, the composite material of one embodiment of the presentinvention has high carrier-generation efficiency and a highcarrier-transport property. Therefore, with the use of the compositematerial of one embodiment of the present invention, it is possible torealize a light-emitting element having high emission efficiency.

In addition, the hydrocarbon compound does not exhibit high absorptionpeak in the visible light region. Furthermore, the hydrocarbon compoundhas a low HOMO level, and absorption due to charge-transfer interactionwith the inorganic compound is unlikely to occur. Thus, the compositematerial of one embodiment of the present invention is unlikely toexhibit an absorption peak in the visible light region, and has a highlight-transmitting property. Therefore, this also shows that with theuse of the composite material of one embodiment of the presentinvention, it is possible to realize a light-emitting element havinghigh emission efficiency.

The composite material of one embodiment of the present invention cansuppress charge accumulation; therefore, a light-emitting element havinga long lifetime can be provided.

There is no limitation on the emission color of a light-emitting elementto which the composite material of one embodiment of the presentinvention is applied. In addition, it does not matter whether alight-emitting element to which the composite material of one embodimentof the present invention is applied exhibits fluorescence orphosphorescence. In any light-emitting element, the composite materialof one embodiment of the present invention hardly causes absorption ofemission energy and reduction of efficiency, and thus can be suitablyused for a hole-injection layer.

The hole-transport layer 702 is a layer that contains a substance havinga high hole-transport property. As a material of the hole-transportlayer 702, the hydrocarbon compound used for the composite material ofone embodiment of the present invention may be used. Other examples ofthe substance having a high hole-transport property are aromatic aminecompounds such as 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl(abbreviation: NPB or α-NPB),N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine(abbreviation: TPD), 4-phenyl-4′-(9-phenylfluoren-9-yl)triphenylamine(abbreviation: BPAFLP),4,4′-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl(abbreviation: DFLDPBi), and4,4′-bis[N-(spiro-9,9′-bifluoren-2-yl)-N-phenylamino]biphenyl(abbreviation: BSPB). The substances mentioned here are mainlysubstances that have a hole mobility of 10⁻⁶ cm²/Vs or more. Note thatother than these substances, any substance that has a property oftransporting more holes than electrons may be used. Note that the layercontaining a substance having a high hole-transport property is notlimited to a single layer, and may be a stack of two or more layerscontaining any of the above substances.

For the hole-transport layer 702, a carbazole derivative such as4,4′-di(N-carbazolyl)biphenyl (abbreviation: CBP),9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), or9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation:PCzPA) or an anthracene derivative such as2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA),9,10-di(2-naphthyl)anthracene (abbreviation: DNA), or9,10-diphenylanthracene (abbreviation: DPAnth) may be used.

In particular, the hydrocarbon compound in the composite material of oneembodiment of the present invention has a low HOMO level; therefore, amaterial having a low HOMO level can be used also for the hole-transportlayer. With such a structure, it is possible to prevent chargeaccumulation at the interface between the light-emitting layer and thehole-transport layer, and it is possible to extend the lifetime of thelight-emitting element. Specifically, for the hole-transport layer, aHOMO level lower than or equal to −5.6 eV is preferred. From such apoint of view, as a compound that is used for the hole-transport layer,a carbazole derivative, a dibenzothiophene derivative, a dibenzofuranderivative, an anthracene derivative, or the like is preferable.Alternatively, the hydrocarbon compound used for the composite materialof one embodiment of the present invention may be used. In thisstructure, the hydrocarbon compound used for the composite material ofone embodiment of the present invention is preferably used for thehole-injection layer and the hole-transport layer, in which case theHOMO levels are close to each other to reduce carrier injection barrier.The hydrocarbon compound used for the composite material of oneembodiment of the present invention which is used for the hole-injectionlayer and the hydrocarbon compound used for the hole-transport layer areparticularly preferably the same materials. Preferably, the hydrocarboncompound used for the composite material of one embodiment of thepresent invention is used for the hole-transport layer and thelight-emitting layer is provided in contact with the hole-transportlayer, in which case an element with high reliability can be obtained.

Note that for the hole-transport layer 702, a high molecular compoundsuch as poly(N-vinylcarbazole) (abbreviation: PVK),poly(4-vinyltriphenylamine) (abbreviation: PVTPA),poly[N-(4-{N′-[4-(4-diphenylamino)phenyl]phenyl-N′-phenylamino}phenyl)methacrylamide](abbreviation: PTPDMA), orpoly[N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine] (abbreviation:Poly-TPD) can also be used.

The light-emitting layer 703 is a layer that contains a light-emittingorganic compound. As the light-emitting organic compound, for example, afluorescent compound which emits fluorescence or a phosphorescentcompound which emits phosphorescence can be used.

Examples of a fluorescent compound that can be used for thelight-emitting layer 703 are the following light-emitting materials, forexample: materials that emit blue light, such asN,N′-bis[4-(9H-carbazol-9-yl)phenyl]-N,N′-diphenylstilbene-4,4′-diamine(abbreviation: YGA2S),4-(9H-carbazol-9-yl)-4′-(10-phenyl-9-anthryl)triphenylamine(abbreviation: YGAPA), and4-(10-phenyl-9-anthryl)-4′-(9-phenyl-9H-carbazol-3-yl)triphenylamine(abbreviation: PCBAPA); materials that emit green light, such asN-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine(abbreviation: 2PCAPA),N-[9,10-bis(1,1′-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine(abbreviation: 2PCABPhA),N-(9,10-diphenyl-2-anthryl)-N,N′,N-triphenyl-1,4-phenylenediamine(abbreviation: 2DPAPA),N-[9,10-bis(1,1′-biphenyl-2-yl)-2-anthryl]-triphenyl-1,4-phenylenediamine(abbreviation: 2DPABPhA),N-[9,10-bis(1,1′-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine(abbreviation: 2YGABPhA), and N,N,9-triphenylanthracen-9-amine(abbreviation: DPhAPhA); materials that emit yellow light, such asrubrene and 5,12-bis(1,1′-biphenyl-4-yl)-6,11-diphenyltetracene(abbreviation: BPT); and materials that emit red light, such asN,N,N′,N′-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation:p-mPhTD) and7,14-diphenyl-N,N,N′,N′-tetrakis(4-methylphenyl)acenaphtho[1,2-α]fluoranthene-3,10-diamine(abbreviation: p-mPhAFD).

The hydrocarbon compound used for the composite material of oneembodiment of the present invention exhibits purple to bluefluorescence. Therefore, the hydrocarbon compound used for the compositematerial of one embodiment of the present invention can be used as afluorescent compound in the light-emitting layer 703.

Examples of a phosphorescent compound that can be used for thelight-emitting layer 703 are the following light-emitting materials:materials that emit blue light, such asbis[2-(4′,6′-difluorophenyl)pyridinato-N,C^(2′)]iridium(III)tetrakis(1-pyrazolyl)borate(abbreviation: FIr6),bis[2-(4′,6′-difluorophenyl)pyridinato-N,C^(2′)]iridium(III)picolinate(abbreviation: FIrpic),bis{2-[3′,5′-bis(trifluoromethyl)phenyl]pyridinato-N,C^(2′)}iridium(III)picolinate(abbreviation:[Ir(CF₃ppy)₂(pic]), andbis[2-(4′,6′-difluorophenyl)pyridinato-N,C^(2′)]iridium(III)acetylacetonate(abbreviation: FIr(acac]); materials that emit green light, such astris(2-phenylpyridinato-N,C^(2′))iridium(III) (abbreviation: [Ir(ppy)₃),bis(2-phenylpyridinato-N,C^(2′))iridium(III)acetylacetonate(abbreviation:[Ir(ppy)₂(acac]),bis(1,2-diphenyl-1H-benzimidazolato)iridium(III)acetylacetonate(abbreviation: [Ir(pbi)₂(acac]),bis(benzo[h]quinolinato)iridium(III)acetylacetonate (abbreviation:[Ir(bzq)₂(acac]), and tris(benzo[h]quinolinato)iridium(III)(abbreviation: [Ir(bzq)₃); materials that emit yellow light, such asbis(2,4-diphenyl-1,3-oxazolato-N,C^(2′))iridium(III)acetylacetonate(abbreviation: [Ir(dpo)₂(acac]),bis[2-(4′-(perfluorophenylphenyl)pyridinato]iridium(III)acetylacetonate(abbreviation: [Ir(p-PF-ph)₂(acac]),bis(2-phenylbenzothiazolato-N,C^(2′))iridium(III)acetylacetonate(abbreviation: [Ir(bt)₂(acac]),(acetylacetonato)bis[2,3-bis(4-fluorophenyl)-5-methylpyrazinato]iridium(III)(abbreviation: [Ir(Fdppr-Me)₂(acac]), and (acetylacetonato)bis{2-(4-methoxyphenyl)-3,5-dimethylpyrazinato}iridium(III) (abbreviation:[Ir(dmmoppr)₂(acac]); materials that emit orange light, such astris(2-phenylquinolinato-N,C^(2′))iridium(III) (abbreviation: [Ir(pq)₃),bis(2-phenylquinolinato-N,C^(2′))iridium(III)acetylacetonate(abbreviation: [Ir(pq)₂(acac]),(acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III)(abbreviation: [Ir(mppr-Me)₂(acac]), and(acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium(III)(abbreviation: [Ir(mppr-iPr)₂(acac]); and materials that emit red light,for example, organometallic complexes, such asbis[2-(2′-benzo[4,5-α]thienyl)pyridinato-N,C^(3′))iridium(III)acetylacetonate(abbreviation: [Ir(btp)₂(acac]),bis(1-phenylisoquinolinato-N,C^(2′))iridium(III)acetylacetonate(abbreviation: [Ir(piq)₂(acac),(acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III)(abbreviation: [Ir(Fdpq)₂(acac]),(acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III)(abbreviation: [Ir(tppr)₂(acac]),(dipivaloylmethanato)bis(2,3,5-triphenylpyrazinato)iridium(III)(abbreviation: [Ir(tppr)₂(dpm]), and(2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin)platinum(II)(abbreviation: PtOEP). Any of the following rare earth metal complexescan be used as a phosphorescent compound:tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation:Tb(acac)₃(Phen]);tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III)(abbreviation: Eu(DBM)₃(Phen]); andtris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III)(abbreviation: Eu(TTA)₃(Phen]), because their light emission is from arare earth metal ion (electronic transition between differentmultiplicities) in such a rare earth metal complex.

Note that the light-emitting layer 703 may have a structure in which anyof the above-described light-emitting organic compounds (a guestmaterial) is dispersed into another substance (a host material). Avariety of substances can be used as the host material, and it ispreferable to use a substance that has a lowest unoccupied molecularorbital level (LUMO level) higher than that of a guest material and hasa HOMO level lower than that of the guest material. In the case wherethe guest material is a fluorescent compound, the host materialpreferably has a high singlet excitation energy level (S1 level). In thecase where the guest material is a phosphorescent compound, the hostmaterial preferably has a high triplet excitation energy level (T1level).

The hydrocarbon compound used for the composite material of oneembodiment of the present invention has a high LUMO level, a low HOMOlevel, a high S1 level, and a high T1 level. Therefore, the hydrocarboncompound can be used the host material, and specifically as a hostmaterial for a fluorescent compound which emits visible light or aphosphorescent compound which emits yellow light or light having alonger wavelength than yellow light.

Specific examples of the host material that can be used are thefollowing materials: metal complexes, such astris(8-quinolinolato)aluminum(III) (abbreviation: Alq),tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq₃),bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq₂),bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III)(abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq),bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), andbis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ);heterocyclic compounds, such as2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation:PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene(abbreviation: OXD-7),3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole(abbreviation: TAZ),2,2′,2″-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole)(abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), andbathocuproine (BCP); condensed aromatic compounds, such as9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA),3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole(abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene(abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA),2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA),9,9′-bianthryl (abbreviation: BANT),9,9′-(stilbene-3,3′-diyl)diphenanthrene (abbreviation: DPNS),9,9′-(stilbene-4,4′-diyl)diphenanthrene (abbreviation: DPNS2),3,3′,3″-(benzene-1,3,5-triyl)tripyrene (abbreviation: TPB3),9,10-diphenylanthracene (abbreviation: DPAnth), and6,12-dimethoxy-5,11-diphenylchrysene; aromatic amine compounds, such asN,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine(abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine(abbreviation: DPhPA),N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine(abbreviation: PCAPA),N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine(abbreviation: PCAPBA),N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine(abbreviation: 2PCAPA), NPB (or α-NPD), TPD, DFLDPBi, and BSPB; and thelike.

Plural kinds of host materials can also be used. For example, in orderto suppress crystallization, a substance such as rubrene whichsuppresses crystallization, may be further added. In addition, in orderto transfer energy or transport carriers to the guest material moreefficiently, a material having a high hole mobility (e.g., a materialhaving an amine skeleton, such as NPB, or a material having a carbazoleskeleton, such as CBP) or a material having a high electron mobility(e.g., a material having a heterocyclic skeleton, such as Alq) may befurther added.

With a structure in which a guest material is dispersed in a hostmaterial, crystallization of the light-emitting layer 703 can besuppressed. In addition, concentration quenching due to highconcentration of the guest material can also be suppressed.

For the light-emitting layer 703, a high molecular compound can be used.Specific examples of materials that emit blue light arepoly(9,9-dioctylfluorene-2,7-diyl) (abbreviation: PFO),poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,5-dimethoxybenzene-1,4-diyl)](abbreviation: PF-DMOP), poly{(9,9-dioctylfluorene-2,7-diyl)-co-[N,N′-di-(p-butylphenyl)-1,4-diaminobenzene]}(abbreviation: TAB-PFH), and the like. Specific examples of materialsthat emit green light are poly(p-phenylenevinylene) (abbreviation: PPV),poly[(9,9-dihexylfluorene-2,7-diyl)-alt-co-(benzo[2,1,3]thiadiazole-4,7-diyl)](abbreviation: PFBT),poly[(9,9-dioctyl-2,7-divinylenefluorenylene)-alt-co-(2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene)],and the like. Specific examples of materials that emit red orange tolight are poly[2-methoxy-5-(2′-ethylhexoxy)-1,4-phenylenevinylene](abbreviation: MEH-PPV), poly(3-butylthiophene-2,5-diyl) (abbreviation:R4-PAT), poly{[9,9-dihexyl-2,7-bis(1-cyanovinylene)fluorenylene]-alt-co-[2,5-bis(N,N′-diphenylamino)-1,4-phenylene]}, poly{[2-methoxy-5-(2-ethylhexyloxy)-1,4-bis(1-cyanovinylenephenylene)]-alt-co-[2,5-bis(N,N′-diphenylamino)-1,4-phenylene]}(abbreviation: CN-PPV-DPD), and the like.

Further, by providing a plurality of light-emitting layers and makingemission colors of the light-emitting layers different, light emissionof a desired color can be obtained from the light-emitting element as awhole. For example, the emission colors of first and secondlight-emitting layers are complementary in a light-emitting elementhaving the two light-emitting layers, so that the light-emitting elementcan be made to emit white light as a whole. Note that the term“complementary” means color relationship in which an achromatic color isobtained when colors are mixed. That is, emission of white light can beobtained by mixture of light emitted from substances whose emissioncolors are complementary colors. Further, the same applies to alight-emitting element having three or more light-emitting layers.

The electron-transport layer 704 is a layer that contains a substancehaving a high electron-transport property. Examples of the substancehaving a high electron-transport property are metal complexes having aquinoline skeleton or a benzoquinoline skeleton, such astris(8-quinolinolato)aluminum (abbreviation: Alq),tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq₃),bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq₂), andbis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (abbreviation:BAlq). Other examples are metal complexes having an oxazole-based orthiazole-based ligand, such as bis[2-(2-hydroxyphenyl)benzoxazolato]zinc(abbreviation: Zn(BOX)₂) and bis[2-(2-hydroxyphenyl)benzothiazolato]zinc(abbreviation: Zn(BTZ)₂). Other than metal complexes,2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation:PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene(abbreviation: OXD-7),3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole(abbreviation: TAZ), bathophenanthroline (abbreviation: BPhen),bathocuproine (abbreviation: BCP), or the like can be used. Thesubstances described here are mainly substances having an electronmobility of 10⁻⁶ cm²/Vs or more. Further, the electron-transport layeris not limited to a single layer, and may be a stack of two or morelayers containing any of the above substances.

The electron-injection layer 705 is a layer that contains a substancehaving a high electron-injection property. Examples of the substancethat can be used for the electron-injection layer 705 are alkali metals,alkaline earth metals, and compounds thereof, such as lithium, cesium,calcium, lithium fluoride, cesium fluoride, calcium fluoride, andlithium oxide, rare earth metal compounds, such as erbium fluoride, andthe above-mentioned substances for forming the electron-transport layer704.

Note that the hole-injection layer 701, the hole-transport layer 702,the light-emitting layer 703, the electron-transport layer 704, and theelectron-injection layer 705 which are described above can each beformed by a method, such as an evaporation method (e.g., a vacuumevaporation method), an inkjet method, or a coating method.

In a light-emitting element illustrated in FIG. 2A, the EL layer 102 isprovided between a pair of electrodes, the first electrode 101 and thesecond electrode 108, over the substrate 100. The EL layer 102 includesthe hole-injection layer 701, the hole-transport layer 702, thelight-emitting layer 703, the electron-transport layer 704, and theelectron-injection layer 705. The light-emitting element in FIG. 2Aincludes the second electrode 108 functioning as a cathode over thesubstrate 100, the electron-injection layer 705, the electron-transportlayer 704, the light-emitting layer 703, the hole-transport layer 702,and the hole-injection layer 701 which are stacked over the secondelectrode 108 in this order, and the first electrode 101 providedthereover which functions as an anode.

Furthermore, by making emission colors of EL layers different, light ofa desired color can be obtained from the light-emitting element as awhole. For example, the emission colors of first and second EL layersare complementary in a light-emitting element having the two EL layers,so that the light-emitting element can be made to emit white light as awhole. Further, the same applies to a light-emitting element havingthree or more EL layers.

A plurality of EL layers may be stacked between the first electrode 101and the second electrode 108, as illustrated in FIG. 1B. In that case, acharge-generation layer 803 is preferably provided between a first ELlayer 800 and a second EL layer 801 which are stacked. Thecharge-generation layer 803 can be formed using the composite materialof one embodiment of the present invention. The composite material ofone embodiment of the present invention has high carrier generationefficiency and a high hole-transport property at the time of voltageapplication. Therefore, with the use of the composite material of oneembodiment of the present invention, it is possible to realize alight-emitting element having a low driving voltage. In addition, it ispossible to realize a light-emitting element having high emissionefficiency.

Also in this case, the hydrocarbon compound used for the compositematerial of one embodiment of the present invention can be suitably usedfor the hole-transport layer in contact with the layer containing thecomposite material of one embodiment of the present invention or for thelight-emitting layer in contact with the hole-transport layer.

In addition, the hydrocarbon compound exhibits no absorption peak in thevisible light region. Furthermore, the hydrocarbon compound has a lowHOMO level, and absorption due to charge-transfer interaction with theinorganic compound is unlikely to occur. Thus, the composite material ofone embodiment of the present invention is unlikely to exhibit anabsorption peak in the visible light region, and has a highlight-transmitting property. Therefore, this also shows that with theuse of the composite material of one embodiment of the presentinvention, it is possible to realize a light-emitting element havinghigh emission efficiency.

Further, the charge-generation layer 803 may have a stacked structureincluding a layer containing the composite material of one embodiment ofthe present invention and a layer containing another material. In thatcase, as the layer containing another material, a layer containing anelectron-donating substance and a substance with a highelectron-transport property, a layer formed of a transparent conductivefilm, or the like can be used. As for a light-emitting element havingsuch a structure, problems such as energy transfer and quenching hardlyoccur, and a light-emitting element which has both high emissionefficiency and a long lifetime can be easily obtained due to expansionin the choice of materials. Moreover, a light-emitting element whichprovides phosphorescence from one of the EL layers and fluorescence fromthe other of the EL layers can be readily obtained. Note that thisstructure can be combined with the above-described structures of the ELlayer.

Similarly, a light-emitting element in which three or more EL layers 802are stacked as illustrated in FIG. 2B can also be employed. As in thelight-emitting element according to this embodiment, when a plurality ofEL layers with a charge-generation layer interposed therebetween isprovided between a pair of electrodes, it is possible to realize anelement having a long lifetime which can emit light at a high luminancewhile current density is kept low.

As illustrated in FIG. 1C, the EL layer may include the hole-injectionlayer 701, the hole-transport layer 702, the light-emitting layer 703,the electron-transport layer 704, an electron-injection buffer layer706, an electron-relay layer 707, and a composite material layer 708which is in contact with the second electrode 108, between the firstelectrode 101 and the second electrode 108.

It is preferable to provide the composite material layer 708 which is incontact with the second electrode 108, in which case damage caused tothe EL layer 102 particularly when the second electrode 108 is formed bya sputtering method can be reduced. The composite material layer 708 canbe formed using the composite material of one embodiment of the presentinvention.

Further, since the above composite material layer 708 functions as acharge generation layer, carriers can be favorably injected from thesecond electrode 108 into the electron-relay layer 707 by passingthrough the composite material layer 708.

Further, by providing the electron-injection buffer layer 706, aninjection barrier between the composite material layer 708 and theelectron-transport layer 704 can be reduced; thus, electrons generatedin the composite material layer 708 can be easily injected into theelectron-transport layer 704.

A substance having a high electron-injection property, such as an alkalimetal, an alkaline earth metal, a rare earth metal, a compound of theabove metal (e.g., an alkali metal compound (e.g., an oxide such aslithium oxide, a halide, and a carbonate such as lithium carbonate orcesium carbonate), an alkaline earth metal compound (e.g., an oxide, ahalide, and a carbonate), or a rare earth metal compound (e.g., anoxide, a halide, and a carbonate), can be used for theelectron-injection buffer layer 706.

Further, in the case where the electron-injection buffer layer 706contains a substance having a high electron-transport property and adonor substance, the donor substance is preferably added so that themass ratio of the donor substance to the substance having a highelectron-transport property ranges from 0.001:1 to 0.1:1. Note that asthe donor substance, an organic compound such as tetrathianaphthacene(abbreviation: TTN), nickelocene, or decamethylnickelocene can be usedas well as an alkali metal, an alkaline earth metal, a rare earth metal,a compound of the above metal (e.g., an alkali metal compound (includingan oxide of lithium oxide or the like, a halide, and a carbonate such aslithium carbonate or cesium carbonate), an alkaline earth metal compound(including an oxide, a halide, and a carbonate), and a rare earth metalcompound (including an oxide, a halide, and a carbonate). Note that asthe substance having a high electron-transport property, any of the samematerials as the electron-transport layer 704 described above can beused.

Furthermore, it is preferable that the electron-relay layer 707 beformed between the electron-injection buffer layer 706 and the compositematerial layer 708. The electron-relay layer 707 is not necessarilyprovided; however, by providing the electron-relay layer 707 having ahigh electron-transport property, electrons can be rapidly transportedto the electron-injection buffer layer 706.

The structure in which the electron-relay layer 707 is interposedbetween the composite material layer 708 and the electron-injectionbuffer layer 706 is a structure in which the acceptor substancecontained in the composite material layer 708 and the donor substancecontained in the electron-injection buffer layer 706 are less likely tointeract with each other, and thus their functions hardly interfere witheach other. Therefore, an increase in driving voltage can be suppressed.

The electron-relay layer 707 contains a substance having a highelectron-transport property and is formed so that the LUMO level of thesubstance having a high electron-transport property is located betweenthe LUMO level of the acceptor substance contained in the compositematerial layer 708 and the LUMO level of the substance having a highelectron-transport property contained in the electron-transport layer704. In the case where the electron-relay layer 707 contains a donorsubstance, the donor level of the donor substance is controlled so as tobe located between the LUMO level of the acceptor substance contained inthe composite material layer 708 and the LUMO level of the substancehaving a high electron-transport property contained in theelectron-transport layer 704. As a specific value of the energy level,the LUMO level of the substance having a high electron-transportproperty contained in the electron-relay layer 707 is preferably higherthan or equal to −5.0 eV, more preferably higher than or equal to −5.0eV and lower than or equal to −3.0 eV.

As the substance having a high electron-transport property contained inthe electron-relay layer 707, a phthalocyanine-based material or a metalcomplex having a metal-oxygen bond and an aromatic ligand is preferablyused.

As the phthalocyanine-based material contained in the electron-relaylayer 707, for example, any of CuPc, a phthalocyanine tin(II) complex(SnPc), a phthalocyanine zinc complex (ZnPc), cobalt(II) phthalocyanine,β-form (CoPc), phthalocyanine iron (FePc), and vanadyl2,9,16,23-tetraphenoxy-29H,31H-phthalocyanine (PhO-VOPc), is preferablyused.

As the metal complex having a metal-oxygen bond and an aromatic ligand,which is contained in the electron-relay layer 707, a metal complexhaving a metal-oxygen double bond is preferably used. The metal-oxygendouble bond has an acceptor property (a property of easily acceptingelectrons); thus, electrons can be transferred (donated and accepted)more easily. Further, the metal complex having a metal-oxygen doublebond is considered stable. Thus, the use of the metal complex having themetal-oxygen double bond enables the light-emitting element to be drivenmore stably at low voltage.

As the metal complex having a metal-oxygen bond and an aromatic ligand,a phthalocyanine-based material is preferable. Specifically, any ofvanadyl phthalocyanine (VOPc), a phthalocyanine tin(IV) oxide complex(SnOPc), and a phthalocyanine titanium oxide complex (TiOPc) ispreferable because a metal-oxygen double bond is likely to act onanother molecular in terms of a molecular structure and an acceptorproperty is high.

Note that as the phthalocyanine-based materials described above, aphthalocyanine-based material having a phenoxy group is preferable.Specifically, a phthalocyanine derivative having a phenoxy group, suchas PhO-VOPc, is preferable. The phthalocyanine derivative having aphenoxy group is soluble in a solvent; thus, the phthalocyaninederivative has an advantage of being easily handled during formation ofa light-emitting element and an advantage of facilitating maintenance ofan apparatus used for film formation.

The electron-relay layer 707 may further contain a donor substance. Asthe donor substance, an organic compound such as tetrathianaphthacene(abbreviation: TTN), nickelocene, or decamethylnickelocene can be usedas well as an alkali metal, an alkaline earth metal, a rare earth metal,and a compound of the above metal (e.g., an alkali metal compound(including an oxide such as lithium oxide, a halide, and a carbonatesuch as lithium carbonate or cesium carbonate), an alkaline earth metalcompound (including an oxide, a halide, and a carbonate), and a rareearth metal compound (including an oxide, a halide, and a carbonate)).When such a donor substance is contained in the electron-relay layer707, electrons can be transferred easily and the light-emitting elementcan be driven at lower voltage.

In the case where a donor substance is contained in the electron-relaylayer 707, other than the materials described above as the substancehaving a high electron-transport property, a substance having a LUMOlevel higher than the acceptor level of the acceptor substance containedin the composite material layer 708 can be used. Specifically, it ispreferable to use a substance having a LUMO level higher than or equalto −5.0 eV, preferably higher than or equal to −5.0 eV and lower than orequal to −3.0 eV. As examples of such a substance, a perylenederivative, a nitrogen-containing condensed aromatic compound, and thelike are given. Note that a nitrogen-containing condensed aromaticcompound is preferably used for the electron-relay layer 707 because ofits stability.

Specific examples of the perylene derivative are3,4,9,10-perylenetetracarboxylic dianhydride (abbreviation: PTCDA),3,4,9,10-perylenetetracarboxylic-bis-benzimidazole (abbreviation:PTCBI), N,N′-dioctyl-3,4,9,10-perylenetetracarboxylic diimide(abbreviation: PTCDI-C8H), N,N′-dihexyl-3,4,9,10-perylenetetracarboxylicdiimide (abbreviation: Hex PTC), and the like.

Specific examples of the nitrogen-containing condensed aromatic compoundare pirazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile(abbreviation: PPDN),2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation:HAT(CN)₆), 2,3-diphenylpyrido[2,3-b]pyrazine (abbreviation: 2PYPR),2,3-bis(4-fluorophenyl)pyrido[2,3-b]pyrazine (abbreviation: F2PYPR), andthe like. Besides, 7,7,8,8-tetracyanoquinodimethane (abbreviation:TCNQ), 1,4,5,8-naphthalenetetracarboxylic dianhydride (abbreviation:NTCDA), perfluoropentacene, copper hexadecafluorophthalocyanine(abbreviation: F₁₆CuPc),N,N′-bis(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyl)-1,4,5,8-naphthalenetetracarboxylicdiimide (abbreviation: NTCDI-C8F),3′,4′-dibutyl-5,5″-bis(dicyanomethylene)-5,5″-dihydro-2,2′:5′,2″-terthiophen(abbreviation: DCMT), methanofullerene (e.g., [6,6]-phenyl C₆₁ butyricacid methyl ester), or the like can be used.

Note that in the case where a donor substance is contained in theelectron-relay layer 707, the electron-relay layer 707 may be formed bya method such as co-evaporation of the substance having a highelectron-transport property and the donor substance.

The hole-injection layer 701, the hole-transport layer 702, thelight-emitting layer 703, and the electron-transport layer 704 can eachbe formed using any of the above-described materials. In particular, thehole-injection layer 701 can be formed using the composite material ofone embodiment of the present invention. Further, the hydrocarboncompound used for the composite material of one embodiment of thepresent invention can be suitably used for each of the hole-transportlayer 702 and the light-emitting layer 703.

Note that this embodiment can be implemented in appropriate combinationwith any of the other embodiments.

Embodiment 3

In this embodiment, a light-emitting device including a light-emittingelement of one embodiment of the present invention is described withreference to FIGS. 3A and 3B. Note that FIG. 3A is a top viewillustrating the light-emitting device, and FIG. 3B is a cross-sectionalview taken along lines A-B and C-D of FIG. 3A.

The light-emitting device of this embodiment includes a source sidedriver circuit 401 and a gate side driver circuit 403 which are drivercircuit portions, a pixel portion 402, a sealing substrate 404, asealing material 405, a flexible printed circuit (FPC) 409, and anelement substrate 410. A portion enclosed by the sealing material 405 isa space.

A lead wiring 408 is a wiring for transmitting signals that are to beinput to the source side driver circuit 401 and the gate side drivercircuit 403, and receives a video signal, a clock signal, a startsignal, a reset signal, and the like from the FPC 409 which serves as anexternal input terminal. Although only the FPC is illustrated here, aprinted wiring board (PWB) may be attached to the FPC. Thelight-emitting device in this specification includes not only alight-emitting device itself but also a light-emitting device to whichan FPC or a PWB is attached.

The driver circuit portion and the pixel portion are formed over theelement substrate 410 illustrated in FIG. 3A. In FIG. 3B, the sourceside driver circuit 401 which is the driver circuit portion and onepixel in the pixel portion 402 are illustrated.

Note that as the source side driver circuit 401, a CMOS circuit whichincludes an n-channel TFT 423 and a p-channel TFT 424 is formed. Thedriver circuit may be any of a variety of circuits formed with TFTs,such as a CMOS circuit, a PMOS circuit, or an NMOS circuit. Although adriver-integrated type in which a driver circuit is formed over thesubstrate is described in this embodiment, the present invention is notlimited to this type, and the driver circuit can be formed outside thesubstrate.

The pixel portion 402 includes a plurality of pixels having a switchingTFT 411, a current control TFT 412, and a first electrode 413electrically connected to a drain of the current control TFT 412. Notethat an insulator 414 is formed to cover an end portion of the firstelectrode 413. Here, the insulator 414 is formed by using a positivetype photosensitive acrylic resin film.

In order to improve coverage, the insulator 414 is provided such thateither an upper end portion or a lower end portion of the insulator 414has a curved surface with a curvature. For example, when positivephotosensitive acrylic is used as a material for the insulator 414, itis preferable that only an upper end portion of the insulator 414 have acurved surface with a radius of curvature (0.2 μm to 3 μm). For theinsulator 414, it is also possible to use either a negative type thatbecomes insoluble in an etchant by light irradiation or a positive typethat becomes soluble in an etchant by light irradiation.

An EL layer 416 and a second electrode 417 are formed over the firstelectrode 413. Here, as a material for forming the first electrode 413functioning as the anode, a material having a high work function ispreferably used. For example, it is possible to use a single layer of anITO film, an indium tin oxide film that includes silicon, an indiumoxide film that includes 2 wt % to 20 wt % of zinc oxide, a titaniumnitride film, a chromium film, a tungsten film, a Zn film, a Pt film, orthe like, a stacked layer of a titanium nitride film and a film thatmainly includes aluminum, a three-layer structure of a titanium nitridefilm, a film that mainly includes aluminum, and a titanium nitride film,or the like. Note that, when a stacked layer structure is employed,resistance of a wiring is low and an excellent ohmic contact isobtained.

In addition, the EL layer 416 is formed by any of various methods suchas an evaporation method using an evaporation mask, a dropletdischarging method like an inkjet method, a printing method, and a spincoating method. The EL layer 416 includes the composite material of oneembodiment of the present invention which is described in Embodiment 1.Further, another material contained in the EL layer 416 may be a lowmolecular material, an oligomer, a dendrimer, a high molecular material,or the like.

As a material used for the second electrode 417 which is formed over theEL layer 416 and functions as a cathode, it is preferable to use amaterial having a low work function (e.g., Al, Mg, Li, Ca, or an alloyor a compound thereof such as Mg—Ag, Mg—In, or Al—Li). In order thatlight generated in the EL layer 416 be transmitted through the secondelectrode 417, a stack of a metal thin film having a reduced thicknessand a transparent conductive film (e.g., ITO, indium oxide containing 2wt % to 20 wt % of zinc oxide, indium oxide-tin oxide that includessilicon or silicon oxide, or zinc oxide) is preferably used for thesecond electrode 417.

Further, the sealing substrate 404 is bonded to the element substrate410 with the sealing material 405, so that a light-emitting element 418is provided in the space 407 enclosed by the element substrate 410, thesealing substrate 404, and the sealing material 405. The space 407 isfilled with a filler, and may be filled with an inert gas (such asnitrogen or argon) or the sealing material 405.

Note that an epoxy-based resin is preferably used as the sealingmaterial 405. Such a material preferably allows as little moisture andoxygen as possible to penetrate. As a material used for the sealingsubstrate 404, a plastic substrate formed of fiberglass-reinforcedplastics (FRP), polyvinyl fluoride (PVF), polyester, acrylic, or thelike can be used other than a glass substrate or a quartz substrate.

As described above, the active matrix light-emitting device includingthe light-emitting element of one embodiment of the present inventioncan be obtained.

Further, a light-emitting element of the present invention can be usedfor a passive matrix light-emitting device as well as the above activematrix light-emitting device. FIGS. 4A and 4B illustrate a perspectiveview and a cross-sectional view of a passive matrix light-emittingdevice including a light-emitting element of the present invention. Notethat FIG. 4A is a perspective view of the light-emitting device, andFIG. 4B is a cross-sectional view taken along line X-Y of FIG. 4A.

In FIGS. 4A and 4B, an EL layer 504 is provided between a firstelectrode 502 and a second electrode 503 over a substrate 501. An endportion of the first electrode 502 is covered with an insulating layer505. In addition, a partition layer 506 is provided over the insulatinglayer 505. The sidewalls of the partition layer 506 slope so that adistance between both the sidewalls is gradually narrowed toward thesurface of the substrate. In other words, a cross section taken alongthe direction of the short side of the partition layer 506 istrapezoidal, and the base (a side parallel to the plane of theinsulating layer 505 and in contact with the insulating layer 505) isshorter than the upper side (a side parallel to the plane of theinsulating layer 505 and not being in contact with the insulating layer505). With the partition layer 506 provided in such a way, a defect of alight-emitting element due to crosstalk or the like can be prevented.

Thus, the passive matrix light-emitting device including alight-emitting element of one embodiment of the present invention can beobtained.

Examples of light-emitting devices to which one embodiment of thepresent invention is applied are illustrated in FIGS. 27A to 27C. FIG.27A is a top view illustrating the light-emitting devices, and FIGS. 27Band 27C are cross-sectional views taken along the line E-F of FIG. 27A.

Light-emitting devices 900 illustrated in FIGS. 27A to 27C include alight-emitting element 908 (a first electrode 101, an EL layer 102, anda second electrode 108) over a first substrate 901. The light-emittingelement 908 can be formed using any of the materials described inEmbodiment 2. The EL layer 102 includes any of the composition materialsof embodiments of the present invention.

To the light-emitting devices of this embodiment, any of the followingstructures can be applied: a structure in which a light-emitting elementemits light upward (such a structure is also referred to as top emissionstructure); a structure in which a light-emitting element emits lightupward and downward (such a structure is also referred to as dualemission structure); and a structure in which a light-emitting elementemits light downward (such a structure is also referred to as bottomemission structure).

A light-emitting device having a bottom emission structure isillustrated in FIG. 27B.

The light-emitting device illustrated in FIG. 27B has the firstelectrode 101 over the first substrate 901, the EL layer 102 over thefirst electrode 101, and the second electrode 108 over the EL layer 102.

A first terminal 903 is electrically connected to an auxiliary wiring910 and the first electrode 101, and a second terminal 904 iselectrically connected to the second electrode 108. Further, aninsulating layer 909 is formed between end portions of the firstelectrode 101 and the second electrode 108 and between the auxiliarywiring 910 and the EL layer 102. Note that although a structure in whichthe first electrode 101 is formed over the auxiliary wiring 910 isillustrated in FIG. 27B, a structure in which the auxiliary wiring 910is formed over the first electrode 101 may be possible.

In addition, the first substrate 901 and the second substrate 902 arebonded together by a sealing material 912. Further, a desiccant 911 maybe included between the first substrate 901 and the second substrate902.

Further, the upper and/or lower portions of the first substrate 901 maybe provided with a light extraction structure. As the light extractionstructure, an uneven structure can be provided at an interface throughwhich light is transmitted from the side having a high refractive indexto the side having a low refractive index. A specific example is asfollows: as illustrated in FIG. 27B, a light extraction structure 913 awith minute unevenness is provided between the light-emitting element908 having a high refractive index and the first substrate 901 having alower refractive index, and a light extraction structure 913 b withunevenness is provided between the first substrate 901 and the air.

However, in the light-emitting element, unevenness of the firstelectrode 101 might cause leakage current generation in the EL layer 102formed over the first electrode 101. Therefore, in this embodiment, aplanarization layer 914 having a refractive index higher than or equalto that of the EL layer 102 is provided in contact with the lightextraction structure 913 a. Accordingly, the first electrode 101 can bea flat film, and the leakage current generation in the EL layer due tothe unevenness of the first electrode 101 can be suppressed. Further,because of the light extraction structure 913 a at an interface betweenthe planarization layer 914 and the first substrate 901, light whichcannot be extracted to the air due to total reflection can be reduced,so that the light extraction efficiency of the light-emitting device canbe increased.

The present invention is not limited to the structure in which the firstsubstrate 901, the light extraction structure 913 a, and the lightextraction structure 913 b are different components as in FIG. 27B. Twoor all of these may be formed as one component. The light extractionstructure 913 a may be all formed inside a sealing region.

A light-emitting device having a top emission structure is illustratedin FIG. 27C.

The light-emitting device illustrated in FIG. 27C has the secondelectrode 108 over the first substrate 901, the EL layer 102 over thesecond electrode 108, and the first electrode 101 over the EL layer 102.

The first terminal 903 is electrically connected to the second electrode108, and the second terminal 904 is electrically connected to the firstelectrode 101. Further, the insulating layer 909 is formed between endportions of the first electrode 101 and the second electrode 108.

In addition, the first substrate 901 and the second substrate 902 arebonded together by the sealing material 912. Further, an auxiliarywiring may be formed over the first electrode 101. Furthermore, thedesiccant 911 may be included between the first substrate 901 and thesecond substrate 902. The desiccant 911 is preferably provided at aposition that does not overlap a light-emitting region of alight-emitting element. Alternatively, a desiccant that transmits lightfrom the light-emitting element is preferably used.

Although the light-emitting device 900 illustrated in FIG. 27A isoctagonal, the present invention is not limited to this shape. Thelight-emitting device 900 and the light-emitting element 908 may haveother polygonal shapes or a shape having a curve. As the shape of thelight-emitting device 900, a triangle, a quadrangle, a hexagon, or thelike is particularly preferred. The reason for this is that such a shapeallows a plurality of light-emitting devices 900 to be provided in alimited area without a space therebetween, and also because such a shapeenables effective use of the limited substrate area for formation of thelight-emitting device 900. Further, the number of elements formed overthe substrate is not limited to one and a plurality of elements may beprovided.

As materials of the first substrate 901 and the second substrate 902, amaterial having a light-transmitting property, such as glass, quartz, oran organic resin can be used. At least one of the first substrate 901and the second substrate 902 transmits light emitted from thelight-emitting element.

In the case where an organic resin is used for the substrates, forexample, any of the following can be used as the organic resin:polyester resins such as polyethylene terephthalate (PET) andpolyethylene naphthalate (PEN), a polyacrylonitrile resin, a polyimideresin, a polymethylmethacrylate resin, a polycarbonate (PC) resin, apolyethersulfone (PES) resin, a polyamide resin, a cycloolefin resin, apolystyrene resin, a polyamide imide resin, a polyvinylchloride resin,and the like. A substrate in which a glass fiber is impregnated with anorganic resin or a substrate in which an inorganic filler is mixed withan organic resin can also be used.

The light-emitting devices described in this embodiment (the activematrix light-emitting device and the passive matrix light-emittingdevice) are both formed using a light-emitting element of one embodimentof the present invention, and accordingly, the light-emitting deviceshave low power consumption.

Note that this embodiment can be implemented in appropriate combinationwith any of the other embodiments.

Embodiment 4

In this embodiment, with reference to FIGS. 5A to 5E and FIG. 6,description is given of examples of a variety of electronic devices andlighting devices that are each completed by using a light-emittingdevice which is one embodiment of the present invention.

Examples of the electronic devices to which the light-emitting device isapplied are television devices (also referred to as TV or televisionreceivers), monitors for computers and the like, cameras such as digitalcameras and digital video cameras, digital photo frames, cellular phones(also referred to as portable telephone devices), portable gamemachines, portable information terminals, audio playback devices, largegame machines such as pachinko machines, and the like. Specific examplesof these electronic devices and a lighting device are illustrated inFIGS. 5A to 5E.

FIG. 5A illustrates an example of a television device. In the televisiondevice 7100, a display portion 7103 is incorporated in a housing 7101.The display portion 7103 is capable of displaying images, and alight-emitting device can be used for the display portion 7103. Inaddition, here, the housing 7101 is supported by a stand 7105.

The television device 7100 can be operated with an operation switch ofthe housing 7101 or a separate remote controller 7110. With operationkeys 7109 of the remote controller 7110, channels and volume can becontrolled and images displayed on the display portion 7103 can becontrolled. Furthermore, the remote controller 7110 may be provided witha display portion 7107 for displaying data output from the remotecontroller 7110.

Note that the television device 7100 is provided with a receiver, amodem, and the like. With the receiver, general television broadcastingcan be received. Furthermore, when the television device 7100 isconnected to a communication network by wired or wireless connection viathe modem, one-way (from a transmitter to a receiver) or two-way(between a transmitter and a receiver, between receivers, or the like)data communication can be performed.

FIG. 5B illustrates a computer, which includes a main body 7201, ahousing 7202, a display portion 7203, a keyboard 7204, an externalconnection port 7205, a pointing device 7206, and the like. Thiscomputer is manufactured by using a light-emitting device for thedisplay portion 7203.

FIG. 5C illustrates a portable game machine, which includes twohousings, a housing 7301 and a housing 7302, connected with a jointportion 7303 so that the portable game machine can be opened or closed.A display portion 7304 is incorporated in the housing 7301 and a displayportion 7305 is incorporated in the housing 7302. In addition, theportable game machine illustrated in FIG. 5C includes a speaker portion7306, a recording medium insertion portion 7307, an LED lamp 7308, aninput means (an operation key 7309, a connection terminal 7310, a sensor7311 (a sensor having a function of measuring force, displacement,position, speed, acceleration, angular velocity, rotational frequency,distance, light, liquid, magnetism, temperature, chemical substance,sound, time, hardness, electric field, current, voltage, electric power,radiation, flow rate, humidity, gradient, oscillation, odor, or infraredrays), and a microphone 7312), and the like. It is needless to say thatthe structure of the portable game machine is not limited to the aboveas long as a light-emitting device is used for at least either thedisplay portion 7304 or the display portion 7305, or both, and mayinclude other accessories as appropriate. The portable game machineillustrated in FIG. 5C has a function of reading out a program or datastored in a storage medium to display it on the display portion, and afunction of sharing information with another portable game machine bywireless communication. The portable game machine illustrated in FIG. 5Ccan have a variety of functions without limitation to the above.

FIG. 5D illustrates an example of a cellular phone. The cellular phone7400 is provided with a display portion 7402 incorporated in a housing7401, operation buttons 7403, an external connection port 7404, aspeaker 7405, a microphone 7406, and the like. Note that the cellularphone 7400 is manufactured using a light-emitting device for the displayportion 7402.

When the display portion 7402 of the cellular phone 7400 illustrated inFIG. 5D is touched with a finger or the like, data can be input to thecellular phone 7400. Further, operations such as making a call andcreating e-mail can be performed by touch on the display portion 7402with a finger or the like.

There are mainly three screen modes of the display portion 7402. Thefirst mode is a display mode mainly for displaying an image. The secondmode is an input mode mainly for inputting information such ascharacters. The third mode is a display-and-input mode in which twomodes of the display mode and the input mode are mixed.

For example, in the case of making a call or creating e-mail, acharacter input mode mainly for inputting characters is selected for thedisplay portion 7402 so that characters displayed on a screen can beinput. In this case, it is preferable to display a keyboard or numberbuttons on almost the entire screen of the display portion 7402.

When a detection device including a sensor for detecting inclination,such as a gyroscope or an acceleration sensor, is provided inside thecellular phone 7400, display on the screen of the display portion 7402can be automatically changed by determining the orientation of thecellular phone 7400 (whether the cellular phone is placed horizontallyor vertically for a landscape mode or a portrait mode).

The screen modes are switched by touch on the display portion 7402 oroperation with the operation buttons 7403 of the housing 7401.Alternatively, the screen modes can be switched depending on kinds ofimages displayed on the display portion 7402. For example, when a signalfor an image to be displayed on the display portion is data of movingimages, the screen mode is switched to the display mode. When the signalis text data, the screen mode is switched to the input mode.

Moreover, in the input mode, if a signal detected by an optical sensorin the display portion 7402 is detected and the input by touch on thedisplay portion 7402 is not performed during a certain period, thescreen mode may be controlled so as to be switched from the input modeto the display mode.

The display portion 7402 may function as an image sensor. For example,an image of a palm print, a fingerprint, or the like is taken by touchon the display portion 7402 with the palm or the finger, so thatpersonal identification can be performed. Furthermore, by provision of abacklight or a sensing light source emitting near-infrared light for thedisplay portion, an image of a finger vein, a palm vein, or the like canalso be taken.

FIG. 5E illustrates a desk lamp, which includes a lighting portion 7501,a shade 7502, an adjustable arm 7503, a support 7504, a base 7505, and apower switch 7506. The desk lamp is manufactured using a light-emittingdevice for the lighting portion 7501. Note that the “lighting device”also includes ceiling lights, wall lights, and the like.

FIG. 6 illustrates an example in which a light-emitting device is usedfor an interior lighting device 811. Since the light-emitting device canhave a larger area, it can be used as a lighting device having a largearea. Furthermore, the light-emitting device can be used as a roll-typelighting device 812. As illustrated in FIG. 6, a desk lamp 813 describedwith reference to FIG. 5E may also be used in a room provided with theinterior lighting device 811.

In the above-described manner, electronic devices or lighting devicescan be obtained by application of a light-emitting device. Applicationrange of the light-emitting device is so wide that the light-emittingdevice can be applied to electronic devices in a variety of fields.

Note that the structure described in this embodiment can be combinedwith the structure described in any of the above embodiments asappropriate.

Example 1

In this example, composite materials of one embodiment of the presentinvention are specifically exemplified. The composite materials of oneembodiment of the present invention each include a hydrocarbon compoundwhich has a substituent bonded to a naphthalene skeleton, a phenanthreneskeleton, or a triphenylene skeleton and which has a molecular weightgreater than or equal to 350 and less than or equal to 2000 and aninorganic compound exhibiting an electron-accepting property withrespect to the hydrocarbon compound, in which the substituent has one ormore rings selected from a benzene ring, a naphthalene ring, aphenanthrene ring, and a triphenylene ring.

Table 1 shows the hydrocarbon compounds used in Composition Examples 1to 3 and Comparison Example in this example and the HOMO levels (eV) ofthe hydrocarbon compounds. Note that the HOMO levels are measured byphotoelectron spectroscopy. In addition, structural formulae of thehydrocarbon compounds are illustrated below.

TABLE 1 Hydrocarbon compound HOMO level (eV) Composition Example 1 N3P−5.8 Composition Example 2 Pn3P −5.9 Composition Example 3 P4N −6.0Comparison Example DPAnth −5.7

Further, FIG. 32A shows an absorption spectrum of N3P in a toluenesolution of N3P, and FIG. 32B shows an emission spectrum thereof.Furthermore, FIG. 33A shows an absorption spectrum of Pn3P in a toluenesolution of Pn3P, and FIG. 33B shows an emission spectrum thereof. Theabsorption spectrum was measured using an ultraviolet-visiblespectrophotometer (V-550, produced by JASCO Corporation). Themeasurements were performed in such a way that each solution was put ina quartz cell. Here is shown the absorption spectrum which was obtainedby subtraction of the absorption spectra of quartz and toluene fromthose of quartz and the solution. In each of FIG. 32A and FIG. 33A, thehorizontal axis represents wavelength (nm) and the vertical axisrepresents absorption intensity (arbitrary unit). In each of FIG. 32Band FIG. 33B, the horizontal axis represents wavelength (nm) and thevertical axis represents emission intensity (arbitrary unit). While N3Pexhibits an absorption peak at around 295 nm and an emission wavelengthpeak at 351 nm (at an excitation wavelength of 300 nm), Pn3P exhibits anabsorption peak at around 302 nm and an emission wavelength peak at 356nm and 374 nm (at an excitation wavelength of 303 nm).

It is thus found from the absorption spectra of the hydrocarboncompounds in the toluene solutions, each of which is used for thecomposite material of one embodiment of the present invention, thatabsorption in the visible light region is hardly observed. In addition,since the emission peaks are located at the shorter wavelengths, thehydrocarbon compounds are each found suitable for a material of thehole-transport layer in contact with a light-emitting layer and for ahost material of a light-emitting layer.

The thin films of the hydrocarbon compounds, each of which is used forthe composite material of one embodiment of the present invention, alsoexhibit almost no absorption spectrum in the visible light region, asdescribed later (see FIGS. 7A and 7B, FIGS. 8A and 8B, FIGS. 9A and 9B,and FIGS. 10A and 10B). The fact that both the solution and the thinfilm exhibit almost no absorption in the visible light region indicateseach hydrocarbon compound is suitable for both a film of a singlesubstance and for a film of a mixture with another organic compound.Thus, the hydrocarbon compounds can each be suitably used for any of thecomposite material of one embodiment of the present invention, ahole-transport layer, and a light-emitting layer.

Further, thermophysical properties were measured with a differentialscanning calorimeter (DSC) (Pyris 1 DSC, manufactured by PerkinElmer,Inc.). The glass transition temperature of Pn3P was found to be 202° C.Thus, Pn3P is found to have good thermophysical properties. Therefore,the composite material of one embodiment of the present invention inwhich this material is used is found to have good thermophysicalproperties.

In each of Composition Examples 1 to 3 and Comparison Example,molybdenum oxide was used as the inorganic compound.

The way how the composite materials of embodiments of the presentinvention were prepared are described.

Composition Example 1

First, a glass substrate was fixed to a substrate holder inside a vacuumevaporation apparatus. Then,1-[3,5-di(naphthalen-1-yl)phenyl]naphthalene (abbreviation: N3P) andmolybdenum(VI) oxide were separately put in respectiveresistance-heating evaporation sources, and under reduced pressure,films containing N3P and molybdenum oxide were formed by aco-evaporation method. At this time, N3P and molybdenum(VI) oxide wereco-evaporated such that the mass ratios of N3P to molybdenum oxide were4:2, 4:1, and 4:0.5 (=N3P:molybdenum oxide). Further, the thickness ofeach film was set to 50 nm.

FIGS. 7A and 7B show measurement results of absorption spectra of thethus formed composite films of N3P and molybdenum oxide (CompositionExample 1). In addition, for comparison, an absorption spectrum of afilm of only N3P (50 nm thick) is also shown in the drawings.

Composition Example 2

First, a glass substrate was fixed to a substrate holder inside a vacuumevaporation apparatus. Then,9-[3,5-di(phenanthren-9-yl)phenyl]phenanthrene (abbreviation: Pn3P) andmolybdenum(VI) oxide were separately put in respectiveresistance-heating evaporation sources, and under reduced pressure,films containing Pn3P and molybdenum oxide were formed by aco-evaporation method. At this time, Pn3P and molybdenum(VI) oxide wereco-evaporated such that the mass ratios of Pn3P to molybdenum oxide were4:2, 4:1, and 4:0.5 (=Pn3P:molybdenum oxide). Further, the thickness ofeach film was set to 50 nm.

FIGS. 8A and 8B show measurement results of absorption spectra of thethus formed composite films of Pn3P and molybdenum oxide (CompositionExample 2). In addition, for comparison, an absorption spectrum of afilm of only Pn3P (50 nm thick) is also shown in the drawings.

Composition Example 3

First, a glass substrate was fixed to a substrate holder inside a vacuumevaporation apparatus. Then, 1,2,3,4-tetraphenylnaphthalene(abbreviation: P4N) and molybdenum(VI) oxide were separately put inrespective resistance-heating evaporation sources, and under reducedpressure, films containing P4N and molybdenum oxide were formed by aco-evaporation method. At this time, P4N and molybdenum(VI) oxide wereco-evaporated such that the mass ratios of P4N to molybdenum oxide were4:4, 4:2, and 4:0.5 (=P4N:molybdenum oxide). Further, the thickness ofeach film was set to 50 nm.

FIGS. 9A and 9B show measurement results of absorption spectra of thethus formed composite films of P4N and molybdenum oxide (CompositionExample 3). In addition, for comparison, an absorption spectrum of afilm of only P4N (50 nm thick) is also shown in the drawings.

Comparison Example

First, a glass substrate was fixed to a substrate holder inside a vacuumevaporation apparatus. Then, 9,10-diphenylanthracene (abbreviation:DPAnth) and molybdenum(VI) oxide were separately put in respectiveresistance-heating evaporation sources, and under reduced pressure,films containing DPAnth and molybdenum oxide were formed by aco-evaporation method. At this time, DPAnth and molybdenum(VI) oxidewere co-evaporated such that the mass ratios of DPAnth to molybdenumoxide were 4:2, 4:1, and 4:0.5 (=DPAnth:molybdenum oxide). Further, thethickness of each film was set to 50 nm.

FIGS. 10A and 10B show measurement results of absorption spectra of thethus formed composite films of DPAnth and molybdenum oxide (ComparisonExample). In addition, for comparison, an absorption spectrum of a filmof only DPAnth (50 nm thick) is also shown in the drawings.

In each of FIGS. 7A and 7B, FIGS. 8A and 8B, FIGS. 9A and 9B, and FIGS.10A and 10B, the horizontal axis represents wavelength (nm) and thevertical axis represents absorbance (no unit).

The composite film of DPAnth and molybdenum oxide (DPAnth:molybdenumoxide=4:0.5), which is described in Comparison Example, wascrystallized.

The hydrocarbon compound used in Comparison Example (FIGS. 10A and 10B)has an anthracene skeleton. In a thick film in which the hydrocarboncompound including an anthracene skeleton is used for a compositematerial, slight absorption peaks in the visible light region, whichoriginate from the anthracene skeleton, are observed. On the other hand,each of the composite materials described in Composition Examples 1 to 3(FIGS. 7A and 7B, FIGS. 8A and 8B, and FIGS. 9A and 9B) does not exhibita significant absorption peak in the wavelength region of at least 360nm or more; thus, the composite materials are found to have a highlight-transmitting property.

It is found that the composite materials of embodiments of the presentinvention are materials that have almost no significant absorption peakin the visible light region and have a high light-transmitting property.Further, the composite materials of embodiments of the present inventionexhibited almost no significant absorption peak also in the infraredregion (the wavelength region of 700 nm or more).

The absorption spectra of the composite materials each including thehydrocarbon compound and molybdenum oxide of one embodiment of thepresent invention have substantially the same shape as the absorptionspectrum of the hydrocarbon compound. Almost no significant absorptionpeak in the visible to infrared region is observed even in the case offilms having a high concentration of molybdenum oxide (specifically, thefilms in which the mass ratios of the hydrocarbon compound to molybdenumoxide is 4:2 and 4:4 in Composition Examples). This indicates that inthe composite materials of embodiments of the present invention, lightabsorption due to charge-transfer interaction is unlikely to occur.

Example 2

In this example, a light-emitting element of one embodiment of thepresent invention is described with reference to FIG. 26A. Note thatstructural formulae of the materials used in the above example areomitted here.

The way how a light-emitting element 1 of this example was fabricated isdescribed below.

(Light-Emitting Element 1)

First, a film of indium tin oxide containing silicon oxide (ITSO) wasformed over a glass substrate 1100 by a sputtering method, so that afirst electrode 1101 which functions as an anode was formed. Note thatthe thickness was set to 110 nm and the electrode area was set to 2 mm×2mm.

In pretreatment for forming the light-emitting element over thesubstrate 1100, UV ozone treatment was performed for 370 seconds afterwashing of a surface of the substrate with water and baking that wasperformed at 200° C. for 1 hour.

After that, the substrate was transferred into a vacuum evaporationapparatus where the pressure had been reduced to approximately 10⁻⁴ Pa,and was subjected to vacuum baking at 170° C. for 30 minutes in aheating chamber of the vacuum evaporation apparatus, and then thesubstrate 1100 was cooled down for about 30 minutes.

Next, the substrate 1100 provided with the first electrode 1101 wasfixed to a substrate holder in the vacuum evaporation apparatus so thatthe surface over which the first electrode 1101 was provided faceddownward. The pressure in the vacuum evaporation apparatus was reducedto about 10⁻⁴ Pa. Then, N3P and molybdenum(VI) oxide were co-evaporatedto form a hole-injection layer 1111 over the first electrode 1101. Thethickness of the hole-injection layer 1111 was set to 50 nm, and themass ratio of N3P to molybdenum oxide was adjusted to 4:2(=N3P:molybdenum oxide). Note that the co-evaporation method refers toan evaporation method in which evaporation is carried out from aplurality of evaporation sources at the same time in one treatmentchamber.

Next, over the hole-injection layer 1111, a film of3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN) wasformed to a thickness of 10 nm to form a hole-transport layer 1112.

Furthermore, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene(abbreviation: CzPA) andN,N′-bis(3-methylphenyl)-N,N′-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine(abbreviation: 1,6mMemFLPAPrn) were co-evaporated to form alight-emitting layer 1113 over the hole-transport layer 1112. Here, themass ratio of CzPA to 1,6mMemFLPAPrn was adjusted to 1:0.04(=CzPA:1,6mMemFLPAPrn). In addition, the thickness of the light-emittinglayer 1113 was set to 30 nm.

Further, over the light-emitting layer 1113, a film of CzPA was formedto a thickness of 10 nm to form a first electron-transport layer 1114 a.

Then, over the first electron-transport layer 1114 a, a film ofbathophenanthroline (abbreviation: BPhen) was formed to a thickness of15 nm to form a second electron-transport layer 1114 b.

Further, over the second electron-transport layer 1114 b, a film oflithium fluoride (LiF) was formed by evaporation to a thickness of 1 nmto form an electron-injection layer 1115.

Lastly, an aluminum film was formed by evaporation to a thickness of 200nm as a second electrode 1103 functioning as a cathode. Thus, thelight-emitting element 1 of this example was fabricated.

Note that, in all the above evaporation steps, evaporation was performedby a resistance-heating method.

Table 2 shows element structures of the light-emitting element 1obtained as described above.

TABLE 2 First Second Hole- Hole- Light- electron- electron- Electron-First injection transport emitting transport transport injection Secondelectrode layer layer layer layer layer layer electrode Light- ITSON3P:MoOx PCPN CzPA:1,6mMemFLPAPrn CzPA BPhen LiF Al emitting 110 nm(=4:2) 10 nm (=1:0.04) 10 nm 15 nm 1 nm 200 nm element 1 50 nm 30 nm

In a glove box containing a nitrogen atmosphere, the light-emittingelement 1 was sealed so as not to be exposed to the air. Then, operationcharacteristics of the light-emitting element 1 were measured. Note thatthe measurements were carried out at room temperature (in an atmospherekept at 25° C.).

The luminance versus voltage characteristics of the light-emittingelement 1 are shown in FIG. 11. In FIG. 11, the horizontal axisrepresents voltage (V) and the vertical axis represents luminance(cd/m²). In addition, the current efficiency versus luminancecharacteristics of the element are shown in FIG. 12. In FIG. 12, thehorizontal axis represents luminance (cd/m²) and the vertical axisrepresents current efficiency (cd/A). Further, Table 3 shows the voltage(V), CIE chromaticity coordinates (x, y), current efficiency (cd/A), andexternal quantum efficiency (%) of the light-emitting element 1 at aluminance of 1100 cd/m².

TABLE 3 Chromaticity Current External Voltage coordinates efficiencyquantum efficiency (V) (x, y) (cd/A) (%) Light-emitting 3.3 (0.14, 0.18)11 8.4 element 1

As shown in Table 3, the CIE chromaticity coordinates of thelight-emitting element 1 are (x, y)=(0.14, 0.18) at a luminance of 1100cd/m². This result shows that blue light emission originating from1,6mMemFLPAPrn was obtained from the light-emitting element 1.

As can be seen from FIG. 11 and FIG. 12, the light-emitting element 1has a low driving voltage and high emission efficiency.

Next, the light-emitting element 1 was subjected to a reliability test.Results of the reliability test are shown in FIG. 13. In FIG. 13, thevertical axis represents normalized luminance (%) with an initialluminance of 100% and the horizontal axis represents driving time (h) ofthe element.

In the reliability test, the light-emitting element of this example wasdriven under the conditions where the initial luminance was set to 5000cd/m² and the current density was constant.

FIG. 13 shows that the light-emitting element 1 kept 55% of the initialluminance after 180 hours elapsed. It is found that the light-emittingelement 1 to which one embodiment of the present invention is appliedhas a long lifetime.

The above results suggest that an element having high emissionefficiency can be achieved when the composite material of one embodimentof the present invention is used for the hole-injection layer of thelight-emitting element. The results also suggest that a light-emittingelement having a low driving voltage can be provided when the compositematerial of one embodiment of the present invention is used for thehole-injection layer of the light-emitting element. The results alsosuggest that a light-emitting element having a long lifetime can bemanufactured when the composite material of one embodiment of thepresent invention is used for the hole-injection layer.

Example 3

In this example, a light-emitting element of one embodiment of thepresent invention is described with reference to FIG. 26A. The materialsused in this example are the ones used in the above examples, andtherefore the chemical formulae thereof are omitted here.

The way how a light-emitting element 2 of this example was fabricated isdescribed below.

(Light-Emitting Element 2)

A hole-injection layer 1111 of the light-emitting element 2 was formedby co-evaporating Pn3P and molybdenum(VI) oxide. The thickness of thehole-injection layer 1111 was set to 50 nm, and the mass ratio of Pn3Pto molybdenum oxide was adjusted to 4:2 (=Pn3P:molybdenum oxide).Components other than the hole-injection layer 1111 were fabricated in amanner similar to that of the light-emitting element 1.

Table 4 shows element structures of the light-emitting element 2obtained as described above.

TABLE 4 First Second Hole- Hole- Light- electron- electron- Electron-First injection transport emitting transport transport injection Secondelectrode layer layer layer layer layer layer electrode Light- ITSOPn3P:MoOx PCPN CzPA:1,6mMemFLPAPrn CzPA BPhen LiF Al emitting 110 nm(=4:2) 10 nm (=1:0.04) 10 nm 15 nm 1 nm 200 nm element 2 50 nm 30 nm

In a glove box containing a nitrogen atmosphere, the light-emittingelement 2 was sealed so as not to be exposed to the air. Then, operationcharacteristics of the light-emitting element 2 were measured. Note thatthe measurements were carried out at room temperature (in the atmospherekept at 25° C.).

The luminance versus voltage characteristics of the light-emittingelement 2 are shown in FIG. 14. In FIG. 14, the horizontal axisrepresents voltage (V) and the vertical axis represents luminance(cd/m²). In addition, the current efficiency versus luminancecharacteristics of the element are shown in FIG. 15. In FIG. 15, thehorizontal axis represents luminance (cd/m²) and the vertical axisrepresents current efficiency (cd/A). Further, Table 5 shows the voltage(V), CIE chromaticity coordinates (x, y), current efficiency (cd/A), andexternal quantum efficiency (%) of the light-emitting element 2 at aluminance of 830 cd/m².

TABLE 5 Chromaticity Current External Voltage coordinates efficiencyquantum efficiency (V) (x, y) (cd/A) (%) Light-emitting 3.1 (0.14, 0.17)9.7 7.8 element 2

As shown in Table 5, the CIE chromaticity coordinates of thelight-emitting element 2 are (x, y)=(0.14, 0.17) at a luminance of 830cd/m². This result shows that blue light emission originating from1,6mMemFLPAPrn was obtained from the light-emitting element 2.

As can be seen from FIG. 14 and FIG. 15, the light-emitting element 2has a low driving voltage and high emission efficiency.

Next, the light-emitting element 2 was subjected to a reliability test.Results of the reliability test are shown in FIG. 16. In FIG. 16, thevertical axis represents normalized luminance (%) with an initialluminance of 100% and the horizontal axis represents driving time (h) ofthe element.

In the reliability test, the light-emitting element of this example wasdriven under the conditions where the initial luminance was set to 5000cd/m² and the current density was constant.

FIG. 16 shows that the light-emitting element 2 kept 61% of the initialluminance after 140 hours elapsed. It is found that the light-emittingelement 2 to which one embodiment of the present invention is appliedhas a long lifetime.

The above results suggest that an element having high emissionefficiency can be achieved when the composite material of one embodimentof the present invention is used for the hole-injection layer of thelight-emitting element. The results also suggest that a light-emittingelement having a low driving voltage can be provided when the compositematerial of one embodiment of the present invention is used for thehole-injection layer of the light-emitting element. The results alsosuggest that a light-emitting element having a long lifetime can bemanufactured when the composite material of one embodiment of thepresent invention is used for the hole-injection layer.

Example 4

In this example, a light-emitting element of one embodiment of thepresent invention is described with reference to FIG. 26A. The materialsused in this example are the ones used in the above examples, andtherefore the chemical formulae thereof are omitted here.

The way how a light-emitting element 3 of this example was fabricated isdescribed below.

(Light-Emitting Element 3)

The hole-transport layer 1112 of the light-emitting element 3 was formedby forming a film of N3P to a thickness of 10 nm. Components other thanthe hole-transport layer 1112 were fabricated in a manner similar tothat of the light-emitting element 1.

Table 6 shows element structures of the light-emitting element 3obtained as described above.

TABLE 6 First Second Hole- Hole- Light- electron- electron- Electron-First injection transport emitting transport transport injection Secondelectrode layer layer layer layer layer layer electrode Light- ITSON3P:MoOx N3P CzPA:1,6mMemFLPAPrn CzPA BPhen LiF Al emitting 110 nm(=4:2) 10 nm (=1:0.04) 10 nm 15 nm 1 nm 200 nm element 3 50 nm 30 nm

In a glove box containing a nitrogen atmosphere, the light-emittingelement 3 was sealed so as not to be exposed to the air. Then, operationcharacteristics of the light-emitting element 3 were measured. Note thatthe measurements were carried out at room temperature (in an atmospherekept at 25° C.).

The luminance versus voltage characteristics of the light-emittingelement 3 are shown in FIG. 17. In FIG. 17, the horizontal axisrepresents voltage (V) and the vertical axis represents luminance(cd/m²). In addition, the current efficiency versus luminancecharacteristics of the element are shown in FIG. 18. In FIG. 18, thehorizontal axis represents luminance (cd/m²) and the vertical axisrepresents current efficiency (cd/A). Further, Table 7 shows the voltage(V), CIE chromaticity coordinates (x, y), current efficiency (cd/A), andexternal quantum efficiency (%) of the light-emitting element 3 at aluminance of 1000 cd/m².

TABLE 7 Chromaticity Current External Voltage coordinates efficiencyquantum efficiency (V) (x, y) (cd/A) (%) Light-emitting 3.7 (0.14, 0.18)11 8.4 element 3

As shown in Table 7, the CIE chromaticity coordinates of thelight-emitting element 3 are (x, y)=(0.14, 0.18) at a luminance of 1000cd/m². This result shows that blue light emission originating from1,6mMemFLPAPrn was obtained from the light-emitting element 3.

As can be seen from FIG. 17 and FIG. 18, the light-emitting element 3has high emission efficiency.

Next, the light-emitting element 3 was subjected to a reliability test.Results of the reliability test are shown in FIG. 19. In FIG. 19, thevertical axis represents normalized luminance (%) with an initialluminance of 100% and the horizontal axis represents driving time (h) ofthe element.

In the reliability test, the light-emitting element of this example wasdriven under the conditions where the initial luminance was set to 5000cd/m² and the current density was constant.

FIG. 19 shows that the light-emitting element 3 kept 70% of the initialluminance after 140 hours elapsed. It is found that the light-emittingelement 3 to which one embodiment of the present invention is appliedhas a long lifetime.

The above results suggest that an element having high emissionefficiency can be achieved when the composite material of one embodimentof the present invention is used for the hole-injection layer and use ofthe hydrocarbon compound included in the composite material for thehole-transport layer in the light-emitting element. The results alsosuggest that a light-emitting element having a long lifetime can befabricated when the composite material of one embodiment of the presentinvention is used for the hole-injection layer and use of thehydrocarbon compound included in the composite material for thehole-transport layer.

Example 5

In this example, a light-emitting element of one embodiment of thepresent invention is described with reference to FIG. 26A. The materialsused in this example are the ones used in the above examples, andtherefore the chemical formulae thereof are omitted here.

The way how a light-emitting element 4 of this example was fabricated isdescribed below.

(Light-Emitting Element 4)

The hole-transport layer 1112 of the light-emitting element 4 was formedby forming a film of Pn3P to a thickness of 10 nm. Components other thanthe hole-transport layer 1112 were fabricated in a manner similar tothat of the light-emitting element 2.

Table 8 shows element structures of the light-emitting element 4obtained as described above.

TABLE 8 First Second Hole- Hole- Light- electron- electron- Electron-First injection transport emitting transport transport injection Secondelectrode layer layer layer layer layer layer electrode Light- ITSOPn3P:MoOx Pn3P CzPA:1,6mMemFLPAPrn CzPA BPhen LiF Al emitting 110 nm(=4:2) 10 nm (=1:0.04) 10 nm 15 nm 1 nm 200 nm element 4 50 nm 30 nm

In a glove box containing a nitrogen atmosphere, the light-emittingelement 4 was sealed so as not to be exposed to the air. Then, operationcharacteristics of the light-emitting element 4 were measured. Note thatthe measurements were carried out at room temperature (in an atmospherekept at 25° C.).

The luminance versus voltage characteristics of the light-emittingelement 4 are shown in FIG. 20. In FIG. 20, the horizontal axisrepresents voltage (V) and the vertical axis represents luminance(cd/m²). In addition, the current efficiency versus luminancecharacteristics of the element are shown in FIG. 21. In FIG. 21, thehorizontal axis represents luminance (cd/m²) and the vertical axisrepresents current efficiency (cd/A). Further, Table 9 shows the voltage(V), CIE chromaticity coordinates (x, y), current efficiency (cd/A), andexternal quantum efficiency (%) of the light-emitting element 4 at aluminance of 1000 cd/m².

TABLE 9 Chromaticity Current External Voltage coordinates efficiencyquantum efficiency (V) (x, y) (cd/A) (%) Light-emitting 3.3 (0.14, 0.17)9.4 7.5 element 4

As shown in Table 9, the CIE chromaticity coordinates of thelight-emitting element 4 are (x, y)=(0.14, 0.17) at a luminance of 1000cd/m². This result shows that blue light emission originating from1,6mMemFLPAPrn was obtained from the light-emitting element 4.

As can be seen from FIG. 20 and FIG. 21, the light-emitting element 4has high emission efficiency.

Next, the light-emitting element 4 was subjected to a reliability test.Results of the reliability test are shown in FIG. 22. In FIG. 22, thevertical axis represents normalized luminance (%) with an initialluminance of 100% and the horizontal axis represents driving time (h) ofthe element.

In the reliability test, the light-emitting element of this example wasdriven under the conditions where the initial luminance was set to 5000cd/m² and the current density was constant.

FIG. 22 shows that the light-emitting element 4 kept 64% of the initialluminance after 140 hours elapsed. It is found that the light-emittingelement 4 to which one embodiment of the present invention is appliedhas a long lifetime.

The above results suggest that an element having high emissionefficiency can be achieved when the composite material of one embodimentof the present invention is used for the hole-injection layer and use ofthe hydrocarbon compound included in the composite material for thehole-transport layer in the light-emitting element. The results alsosuggest that a light-emitting element having a long lifetime can befabricated when the composite material of one embodiment of the presentinvention is used for the hole-injection layer and use of thehydrocarbon compound included in the composite material for thehole-transport layer.

Further, the results suggest that the light-emitting element can haveexcellent element characteristics when the composite material of oneembodiment of the present invention is used for the hole-injection layerof the light-emitting element and the hydrocarbon compound which can beused for the composite material of one embodiment of the presentinvention is provided in contact with the composite material in thehole-injection layer. The results also suggest that the light-emittingelement can have excellent element characteristics when the hydrocarboncompound which can be used for the composite material of one embodimentof the present invention is provided in contact with the light-emittinglayer.

The experimental results of the light-emitting elements 1 to 4 inExamples 2 to 5 show that the composite materials of embodiments of thepresent invention can be suitably used for a light-emitting elementwhich exhibits blue fluorescence.

Example 6

In this example, a light-emitting element of one embodiment of thepresent invention is described with reference to FIG. 26A. Note thatstructural formulae of the materials used in the above example areomitted here.

The way how a light-emitting element 5, a light-emitting element 6, anda comparison light-emitting element 7 of this example were fabricated isdescribed below.

(Light-Emitting Element 5)

First, an ITSO film was formed over a glass substrate 1100 by asputtering method, so that the first electrode 1101 which functions asan anode was formed. Note that the thickness was set to 110 nm and theelectrode area was set to 2 mm×2 mm.

In pretreatment for forming the light-emitting element over thesubstrate 1100, UV ozone treatment was performed for 370 seconds afterwashing of a surface of the substrate with water and baking that wasperformed at 200° C. for 1 hour.

After that, the substrate was transferred into a vacuum evaporationapparatus where the pressure had been reduced to approximately 10⁻⁴ Pa,and was subjected to vacuum baking at 170° C. for 30 minutes in aheating chamber of the vacuum evaporation apparatus, and then thesubstrate 1100 was cooled down for about 30 minutes.

Next, the substrate 1100 provided with the first electrode 1101 wasfixed to a substrate holder in the vacuum evaporation apparatus so thatthe surface over which the first electrode 1101 was provided faceddownward. The pressure in the vacuum evaporation apparatus was reducedto about 10⁻⁴ Pa. Then, P4N and molybdenum(VI) oxide were co-evaporatedto form a hole-injection layer 1111 over the first electrode 1101. Thethickness of the hole-injection layer 1111 was set to 40 nm, and themass ratio of P4N to molybdenum oxide was adjusted to 4:2(=P4N:molybdenum oxide).

Next, over the hole-injection layer 1111, a film of4-phenyl-4′-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP)was formed to a thickness of 20 nm to form a hole-transport layer 1112.

Furthermore, 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline(abbreviation: 2mDBTPDBq-II),4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), and(acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III)(abbreviation: [Ir(tBuppm)₂(acac)]) were co-evaporated to form alight-emitting layer 1113 over the hole-transport layer 1112. Here, themass ratio of 2mDBTPDBq-II to NPB and [Ir(tBuppm)₂(acac)] was adjustedto 0.8:0.2:0.05 (=2mDBTPDBq-II:NPB: [Ir(tBuppm)₂(acac)]). In addition,the thickness of the light-emitting layer 1113 was set to 40 nm.

Further, over the light-emitting layer 1113, a film of 2mDBTPDBq-II wasformed to a thickness of 10 nm to form a first electron-transport layer1114 a.

Then, over the first electron-transport layer 1114 a, a film of BPhenwas formed to a thickness of 20 nm to form a second electron-transportlayer 1114 b.

Further, over the second electron-transport layer 1114 b, a film of LiFwas formed by evaporation to a thickness of 1 nm to form theelectron-injection layer 1115.

Lastly, an aluminum film was formed by evaporation to a thickness of 200nm as the second electrode 1103 functioning as a cathode. Thus, thelight-emitting element 5 of this example was fabricated.

Note that, in all the above evaporation steps, evaporation was performedby a resistance-heating method.

(Light-Emitting Element 6)

A hole-injection layer 1111 of the light-emitting element 6 was formedby co-evaporating Pn3P and molybdenum(VI) oxide. The thickness of thehole-injection layer 1111 was set to 40 nm, and the mass ratio of Pn3Pto molybdenum oxide was adjusted to 4:2 (=Pn3P:molybdenum oxide).Components other than the hole-injection layer 1111 were fabricated in amanner similar to that of the light-emitting element 5.

(Comparison Light-Emitting Element 7)

A hole-injection layer 1111 of the comparison light-emitting element 7was formed by co-evaporating DPAnth and molybdenum(VI) oxide. Thethickness of the hole-injection layer 1111 was set to 40 nm, and themass ratio of DPAnth to molybdenum oxide was adjusted to 4:2(=DPAnth:molybdenum oxide). Components other than the hole-injectionlayer 1111 were fabricated in a manner similar to that of thelight-emitting element 5.

Table 10 shows element structures of the light-emitting element 5, thelight-emitting element 6, and the comparison light-emitting element 7formed as described above.

TABLE 10 First Second Hole- Hole- Light- electron- electron- Electron-First injection transport emitting transport transport injection Secondelectrode layer layer layer layer layer layer electrode Light- ITSOP4N:MoOx BPAFLP 2mDBTPDBq-II:NPB:[Ir(tBuppm)₂(acac)] 2mDBTPDBq-II BPhenLiF Al emitting 110 nm (=4:2) 10 nm (=0.8:0.2:0.05) 10 nm 20 nm 1 nm 200nm element 5 40 nm 40 nm Light- ITSO Pn3P:MoOx BPAFLP2mDBTPDBq-II:NPB:[Ir(tBuppm)₂(acac)] 2mDBTPDBq-II BPhen LiF Al emitting110 nm (=4:2) 10 nm (=0.8:0.2:0.05) 10 nm 20 nm 1 nm 200 nm element 6 40nm 40 nm Compar- ITSO DPAnth:MoOx BPAFLP2mDBTPDBq-II:NPB:[Ir(tBuppm)₂(acac)] 2mDBTPDBq-II BPhen LiF Al ison 110nm (=4:2) 10 nm (=0.8:0.2:0.05) 10 nm 20 nm 1 nm 200 nm light- 40 nm 40nm emitting element 7

In a glove box containing a nitrogen atmosphere, these light-emittingelements were sealed so as not to be exposed to the air. Then, operationcharacteristics of these light-emitting elements were measured. Notethat the measurements were carried out at room temperature (in anatmosphere kept at 25° C.).

The luminance versus voltage characteristics of the light-emittingelement 5, the light-emitting element 6, and the comparisonlight-emitting element 7 are shown in FIG. 23. In FIG. 23, thehorizontal axis represents voltage (V) and the vertical axis representsluminance (cd/m²). In addition, the current efficiency versus luminancecharacteristics of the elements are shown in FIG. 24. In FIG. 24, thehorizontal axis represents luminance (cd/m²) and the vertical axisrepresents current efficiency (cd/A). Further, Table 11 shows thevoltage (V), CIE chromaticity coordinates (x, y), current efficiency(cd/A), and external quantum efficiency (%) of each light-emittingelement at a luminance of 1000 cd/m².

TABLE 11 External Chromaticity Lumi- Current quantum Voltage coordinatesnance efficiency efficiency (V) (x, y) (cd/m²) (cd/A) (%) Light-emitting2.8 (0.45, 0.54) 840 69 20 element 5 Light-emitting 2.9 (0.45, 0.55) 89070 20 element 6 Comparison 3.2 (0.45, 0.55) 1100 64 18 light-emittingelement 7

As shown in Table 11, the CIE chromaticity coordinates of thelight-emitting element 5 are (x, y)=(0.45, 0.54) at a luminance of 840cd/m², the CIE chromaticity coordinates of the light-emitting element 6are (x, y)=(0.45, 0.55) at a luminance of 890 cd/m², and the CIEchromaticity coordinates of the comparison light-emitting element 7 are(x, y)=(0.45, 0.55) at a luminance of 1100 cd/m². These results showthat orange light emission originating from [Ir(tBuppm)₂(acac)] wasobtained from the light-emitting elements of this example.

As can be seen from FIG. 23 and FIG. 24, the light-emitting elements 5and 6 have lower driving voltage and higher emission efficiency than thecomparison light-emitting element 7.

Next, the light-emitting elements were subjected to reliability tests.Results of the reliability tests are shown in FIG. 25. In FIG. 25, thevertical axis represents normalized luminance (%) with an initialluminance of 100% and the horizontal axis represents driving time (h) ofthe elements.

In the reliability tests, the light-emitting elements of this examplewere driven under the conditions where the initial luminance was set to5000 cd/m² and the current density was constant.

FIG. 25 shows that the light-emitting element 5 kept 80% of the initialluminance after 150 hours elapsed, the light-emitting element 6 kept 77%of the initial luminance after 150 hours elapsed, and the comparisonlight-emitting element 7 kept 78% of the initial luminance after 150hours elapsed.

It is found that the light-emitting elements 5 and 6 have as highreliability as the comparison light-emitting element 7.

The above results suggest that an element having high emissionefficiency can be achieved when the composite material of one embodimentof the present invention is used for the hole-injection layer of thelight-emitting element which exhibits phosphorescence. The results alsosuggest that a light-emitting element having a low driving voltage canbe provided when the composite material of one embodiment of the presentinvention is used for the hole-injection layer of the light-emittingelement which exhibits phosphorescence. The results also suggest that alight-emitting element having a long lifetime can be manufactured whenthe composite material of one embodiment of the present invention isused for the hole-injection layer of the light-emitting element whichexhibits phosphorescence.

Further, the results suggest that the composite material of oneembodiment of the present invention can be suitably used for thehole-injection layer of the light-emitting element which exhibits orangephosphorescence. It is thus found that the composite material can besuitably used for a light-emitting element which exhibits orange lightor light having a longer wavelength than orange light.

Example 7

In this example, a light-emitting element of one embodiment of thepresent invention is described with reference to FIG. 26B. Structuralformulae of materials used in this example are illustrated below. Notethat structural formulae of the materials used in the above examples areomitted here.

The way how a light-emitting element 8 of this example of this examplewas fabricated is described below.

(Light-Emitting Element 8)

First, an ITSO film was formed over a glass substrate 1100 by asputtering method, so that the first electrode 1101 which functions asan anode was formed. Note that the thickness was set to 110 nm and theelectrode area was set to 2 mm×2 mm.

In pretreatment for forming the light-emitting element over thesubstrate 1100, UV ozone treatment was performed for 370 seconds afterwashing of a surface of the substrate with water and baking that wasperformed at 200° C. for 1 hour.

After that, the substrate was transferred into a vacuum evaporationapparatus where the pressure had been reduced to approximately 10⁻⁴ Pa,and was subjected to vacuum baking at 170° C. for 30 minutes in aheating chamber of the vacuum evaporation apparatus, and then thesubstrate 1100 was cooled down for about 30 minutes.

Next, the substrate 1100 provided with the first electrode 1101 wasfixed to a substrate holder in the vacuum evaporation apparatus so thatthe surface over which the first electrode 1101 was provided faceddownward. The pressure in the vacuum evaporation apparatus was reducedto about 10⁻⁴ Pa. Then, Pn3P and molybdenum(VI) oxide were co-evaporatedto form a first hole-injection layer 1111 a over the first electrode1101. The thickness of the first hole-injection layer 1111 a was set to33 nm, and the mass ratio of Pn3P to molybdenum(VI) oxide was adjustedto 1:0.5 (=Pn3P:molybdenum oxide).

Next, over the first hole-injection layer 1111 a, a film of PCPN wasformed to a thickness of 30 nm to form a first hole-transport layer 1112a.

Next, CzPA and 1,6mMemFLPAPrn were co-evaporated to form a firstlight-emitting layer 1113 a over the first hole transport-layer 1112 a.Here, the mass ratio of CzPA to 1,6mMemFLPAPrn was adjusted to 1:0.05(=CzPA:1,6mMemFLPAPrn). The thickness of the first light-emitting layer1113 a was set to 30 nm.

Next, over the first light-emitting layer 1113 a, a CzPA film was formedto a thickness of 5 nm and a BPhen film was formed to a thickness of 15nm to form a first electron-transport layer 1114 a.

Further, over the first electron-transport layer 1114 a, a film oflithium oxide (Li₂O) was formed by evaporation to a thickness of 0.1 nmto form a first electron-injection layer 1115 a.

After that, over the first electron-injection layer 1115 a, a film ofcopper phthalocyanine (abbreviation: CuPc) was formed by evaporation toa thickness of 2 nm to form an electron-relay layer 1116.

Next, over the electron-relay layer 1116, Pn3P and molybdenum(VI) oxidewere co-evaporated to form a second hole-injection layer 1111 b. Thethickness of the second hole-injection layer 1111 b was set to 40 nm,and the mass ratio of Pn3P to molybdenum oxide was adjusted to 1:0.5(=Pn3P:molybdenum oxide). Note that the second hole-injection layer 1111b of this example functions as the charge-generation layer described inthe above embodiment.

Next, over the second hole-injection layer 1111 b, a PCPN film wasformed to a thickness of 20 nm to form a second hole-transport layer1112 b.

Further, 2mDBTPDBq-II,4-phenyl-4′-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation:PCBA1BP), and (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III)(abbreviation: [Ir(dppm)₂(acac)]) were co-evaporated to form a secondlight-emitting layer 1113 b over the second hole-transport layer 1112 b.Here, the mass ratio of 2mDBTPDBq-II to PCBA1BP and [Ir(dppm)₂(acac)]was adjusted to 0.8:0.2:0.06 (=2mDBTPDBq-II:PCBA1BP:[Ir(dppm)₂(acac)]).In addition, the thickness of the second light-emitting layer 1113 b wasset to 40 nm.

Next, over the second light-emitting layer 1113 b, a film of2mDBTPDBq-II was formed to a thickness of 15 nm and a film of BPhen wasformed to a thickness of 15 nm to form a second electron-transport layer1114 b.

Further, over the second electron-transport layer 1114 b, a film of LiFwas formed to a thickness of 1 nm to form a second electron-injectionlayer 1115 b.

Lastly, an aluminum film was formed by evaporation to a thickness of 200nm as the second electrode 1103 functioning as a cathode. Thus, thelight-emitting element 8 of this example was fabricated.

Note that, in all the above evaporation steps, evaporation was performedby a resistance-heating method.

Table 12 shows element structures of the light-emitting element 8obtained as described above.

TABLE 12 First electrode ITSO 110 nm First hole- First hole- FirstLight- First electron- First electron- Electron injection layertransport layer emitting layer transport layer injection layer relaylayer Pn3P:MoOx(=1:0.5) PCPN CzPA:1,6mMemFLPAPrn CzPA BPhen Li₂O CuPc 33nm 30 nm (=1:0.05) 5 nm 15 nm 0.1 nm 2 nm 30 nm Second hole- Secondhole- Second Light- Second electron- Second electron- Second injectionlayer transport layer emitting layer transport layer injection layerelectrode Pn3P:MoOx(=1:0.5) PCPN 2mDBTPDBq-II:PCBA1BP:Ir(dppm)₂(acac)2mDBTPDBq-II BPhen LiF Al 40 nm 20 nm (=0.8:0.2:0.06) 15 nm 15 nm 1 nm200 nm 40 nm

In a glove box containing a nitrogen atmosphere, the light-emittingelement 8 was sealed so as not to be exposed to the air. Then, operationcharacteristics of the light-emitting element 8 were measured. Note thatthe measurements were carried out at room temperature (in an atmospherekept at 25° C.).

The current efficiency versus luminance characteristics of thelight-emitting element 8 are shown in FIG. 28. In FIG. 28, thehorizontal axis represents luminance (cd/m²) and the vertical axisrepresents current efficiency (cd/A). In addition, the current versusvoltage characteristics are shown in FIG. 29. In FIG. 29, the horizontalaxis represents voltage (V) and the vertical axis represents current(mA). Further, the chromaticity coordinate versus luminancecharacteristics are shown in FIG. 30. In FIG. 30, the horizontal axisrepresents luminance (cd/m²) and the vertical axis representschromaticity coordinates (the x-coordinate and the y-coordinate). Inaddition, FIG. 31 shows an emission spectrum of the light-emittingelement 8 which was obtained by applying a current of 0.1 mA. In FIG.31, the horizontal axis represents wavelength (nm) and the vertical axisrepresents emission intensity (arbitrary unit). Further, Table 13 showsthe voltage (V), CIE chromaticity coordinates (x, y), current efficiency(cd/A), external quantum efficiency (%), and correlated colortemperature (K) of the light-emitting element 8 at a luminance of 890cd/m².

TABLE 13 External Correlated Chromaticity Current quantum color Voltagecoordinates efficiency efficiency temperature (V) (x, y) (cd/A) (%) (K)Light- 5.8 (0.43, 0.38) 86 36 2800 emitting element 8

As shown in Table 13, the CIE chromaticity coordinates of thelight-emitting element 8 are (x, y)=(0.43, 0.38) at a luminance of 890cd/m². Further, FIG. 31 shows that in the light-emitting element 8,emits the blue light-emitting material (1,6mMemFLPAPrn) and the orangelight-emitting material ([Ir(dppm)₂(acac)]) emit light with a goodbalance. In addition, FIG. 30 shows that the light-emitting element 8undergoes a small change in chromaticity which depends on luminance,indicating its excellent carrier balance. Thus, the light-emittingelement 8 is found suitable for use for a lighting device. Furthermore,as shown in Table 3, the correlated color temperature is 2800K. Lightemission with a color close to an incandescent color is obtained fromthe light-emitting element 8, which also indicates the suitability foruse for a lighting device.

The above results suggest that an element having high emissionefficiency can be achieved when the composite material of one embodimentof the present invention is used for the hole-injection layer and thecharge-generation layer in the tandem light-emitting element. Theresults also suggest that a light-emitting element having a low drivingvoltage can be provided when the composite material of one embodiment ofthe present invention is used for the hole-injection layer and thecharge-generation layer in the tandem light-emitting element. Theresults also suggest that the composite material of one embodiment ofthe present invention can be suitably used for the light-emittingelement for exhibiting white light emission.

Example 8

In this example, the composite material of one embodiment of the presentinvention is specifically exemplified. Table 14 shows the hydrocarboncompound used in Composition Example 4 of this example and the HOMOlevel (eV) of the hydrocarbon compound. Note that the HOMO level ismeasured by photoelectron spectroscopy. In addition, the structuralformula of the hydrocarbon compound is illustrated below.

TABLE 14 Hydrocarbon compound HOMO level (eV) Composition Example 4 βN3P−6.0

Further, FIG. 34A shows an absorption spectrum of βN3P in a toluenesolution of βN3P, and FIG. 34B shows an emission spectrum thereof. Theabsorption spectrum was measured using an ultraviolet-visiblespectrophotometer (V-550, produced by JASCO Corporation). Themeasurements were performed in such a way that each solution was put ina quartz cell. Here is shown the absorption spectrum which was obtainedby subtraction of the absorption spectra of quartz and toluene fromthose of quartz and the solution. In FIG. 34A, the horizontal axisrepresents wavelength (nm) and the vertical axis represents absorptionintensity (arbitrary unit). In FIG. 34B, the horizontal axis representswavelength (nm) and the vertical axis represents emission intensity(arbitrary unit). Further, βN3P exhibits an absorption peak at around296 nm and an emission wavelength peak at 363 nm (at an excitationwavelength of 291 nm).

It is thus found from the absorption spectra of the hydrocarboncompounds in the toluene solutions, each of which is used for thecomposite material of one embodiment of the present invention, thatabsorption in the visible light region is hardly observed. In addition,since the emission peaks are located at the shorter wavelengths, thehydrocarbon compounds are each found suitable for a material of thehole-transport layer in contact with a light-emitting layer and for ahost material of a light-emitting layer.

The thin film of the hydrocarbon compound used for the compositematerial of one embodiment of the present invention also exhibits almostno absorption spectrum in the visible light region, which is describedlater (see FIGS. 35A and 35B). The fact that both the solution and thethin film exhibit almost no absorption in the visible light regionindicates the hydrocarbon compound is suitable for both a film of asingle substance and for a film of a mixture. Thus, the hydrocarboncompound can be suitably used for any of the composite material of oneembodiment of the present invention, a hole-transport layer, and alight-emitting layer.

In Composition Example 4, molybdenum oxide was used as the inorganiccompound.

The way how the composite material of one embodiment of the presentinvention was prepared is described.

Composition Example 4

First, a glass substrate was fixed to a substrate holder inside a vacuumevaporation apparatus. Then,2-[3,5-di-(naphthalen-2-yl)-phenyl]-naphthalene (abbreviation: βN3P) andmolybdenum(VI) oxide were separately put in respectiveresistance-heating evaporation sources, and in a vacuum state, filmscontaining βN3P and molybdenum oxide were formed by a co-evaporationmethod. At this time, βN3P and molybdenum oxide were co-evaporated suchthat the mass ratios of βN3P to molybdenum oxide were 4:2, 4:1, and4:0.5 (=βN3P:molybdenum oxide). Further, the thickness of each film wasset to 50 nm.

FIGS. 35A and 35B show measurement results of absorption spectra of thethus formed composite films of βN3P and molybdenum oxide (CompositionExample 4). In addition, for comparison, an absorption spectrum of afilm of only βN3P (50 nm thick) is also shown in the drawings. In eachof FIGS. 35A and 35B, the horizontal axis represents a wavelength (nm)and the vertical axis represents absorbance (no unit).

The composite material described in Composition Example 4 (FIGS. 35A and35B) does not exhibit a significant absorption peak in the wavelengthregion of at least 360 nm or more and is found to have a highlight-transmitting property. It is thus found that the compositematerial of one embodiment of the present invention is a material thathas almost no significant absorption peak in the visible light regionand has a high light-transmitting property. Further, the compositematerial of one embodiment of the present invention exhibited almost nosignificant absorption peak also in the infrared region (the wavelengthregion of 700 nm or more).

The absorption spectrum of the composite material of one embodiment ofthe present invention, which includes the hydrocarbon compound andmolybdenum oxide, has substantially the same shape as the absorptionspectrum of the hydrocarbon compound. Almost no significant absorptionpeak in the visible to infrared region even in the case of a film havinga high concentration of molybdenum oxide (specifically, the film inwhich the mass ratio of the hydrocarbon compound to molybdenum oxide is4:2). This indicates that in the composite material of one embodiment ofthe present invention, light absorption due to charge-transferinteraction is unlikely to occur.

Example 9

In this example, a light-emitting element of one embodiment of thepresent invention is described with reference to FIG. 26A. Note thatstructural formulae of the materials used in the above example areomitted here.

The way how a light-emitting element 9 of this example was fabricated isdescribed below.

(Light-Emitting Element 9)

First, a film of ITSO was formed over a glass substrate 1100 by asputtering method, so that the first electrode 1101 which functions asan anode was formed. Note that the thickness was set to 110 nm and theelectrode area was set to 2 mm×2 mm.

In pretreatment for forming the light-emitting element over thesubstrate 1100, UV ozone treatment was performed for 370 seconds afterwashing of a surface of the substrate with water and baking that wasperformed at 200° C. for 1 hour.

After that, the substrate was transferred into a vacuum evaporationapparatus where the pressure had been reduced to approximately 10⁻⁴ Pa,and was subjected to vacuum baking at 170° C. for 30 minutes in aheating chamber of the vacuum evaporation apparatus, and then thesubstrate 1100 was cooled down for about 30 minutes.

Next, the substrate 1100 provided with the first electrode 1101 wasfixed to a substrate holder in the vacuum evaporation apparatus so thatthe surface over which the first electrode 1101 was provided faceddownward. The pressure in the vacuum evaporation apparatus was reducedto about 10⁻⁴ Pa. Then, βN3P and molybdenum(VI) oxide were co-evaporatedto form a hole-injection layer 1111 over the first electrode 1101. Thethickness of the hole-injection layer 1111 was set to 50 nm, and themass ratio of βN3P to molybdenum oxide was adjusted to 4:2(=βN3P:molybdenum oxide).

Next, over the hole-injection layer 1111, a film of9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation:PCzPA) was formed to a thickness of 10 nm to form a hole-transport layer1112.

Furthermore, CzPA and 1,6mMemFLPAPrn were co-evaporated to form thelight-emitting layer 1113 over the hole-transport layer 1112. Here, themass ratio of CzPA to 1,6mMemFLPAPrn was adjusted to 1:0.04(=CzPA:1,6mMemFLPAPrn). In addition, the thickness of the light-emittinglayer 1113 was set to 30 nm.

Further, over the light-emitting layer 1113, a film of CzPA was formedto a thickness of 10 nm to form the first electron-transport layer 1114a.

Then, over the first electron-transport layer 1114 a, a film of BPhenwas formed to a thickness of 15 nm to form the second electron-transportlayer 1114 b.

Further, over the second electron-transport layer 1114 b, a film of LiFwas formed by evaporation to a thickness of 1 nm to form theelectron-injection layer 1115.

Lastly, an aluminum film was formed by evaporation to a thickness of 200nm as the second electrode 1103 functioning as a cathode. Thus, thelight-emitting element 9 of this example was fabricated.

Note that, in all the above evaporation steps, evaporation was performedby a resistance-heating method.

Table 15 shows element structures of the light-emitting element 9obtained as described above.

TABLE 15 First Second Hole- Hole- Light- electron- electron- Electron-First injection transport emitting transport transport injection Secondelectrode layer layer layer layer layer layer electrode Light- ITSOβN3P:MoOx PCzPA10 nm CzPA:1,6mMemFLPAPrn CzPA BPhen LiF Al emitting 110nm (=4:2) (=1:0.04) 10 nm 15 nm 1 nm 200 nm element 9 50 nm 30 nm

In a glove box containing a nitrogen atmosphere, the light-emittingelement 9 was sealed so as not to be exposed to the air. Then, operationcharacteristics of the light-emitting element 9 were measured. Note thatthe measurements were carried out at room temperature (in an atmospherekept at 25° C.).

The luminance versus voltage characteristics of the light-emittingelement 9 are shown in FIG. 36. In FIG. 36, the horizontal axisrepresents voltage (V) and the vertical axis represents luminance(cd/m²). In addition, the current efficiency versus luminancecharacteristics of the element are shown in FIG. 37. In FIG. 37, thehorizontal axis represents luminance (cd/m²) and the vertical axisrepresents current efficiency (cd/A). Further, Table 16 shows thevoltage (V), CIE chromaticity coordinates (x, y), current efficiency(cd/A), and external quantum efficiency (%) of the light-emittingelement 9 at a luminance of 1100 cd/m².

TABLE 16 External Chromaticity Current quantum Voltage coordinatesLuminance efficiency efficiency (V) (x, y) (cd/m²) (cd/A) (%) Light- 3.1(0.14, 0.18) 1100 7.7 5.8 emitting element 9

As shown in Table 16, the CIE chromaticity coordinates of thelight-emitting element 9 are (x, y)=(0.14, 0.18) at a luminance of 1100cd/m². This result shows that blue light emission originating from1,6mMemFLPAPrn was obtained from the light-emitting element 9.

As can be seen from FIG. 36 and FIG. 37, the light-emitting element 9has a low driving voltage and high emission efficiency.

The above results suggest that an element having high emissionefficiency can be achieved when the composite material of one embodimentof the present invention is used for the hole-injection layer of thelight-emitting element. The results also suggest that a light-emittingelement having a low driving voltage can be provided when the compositematerial of one embodiment of the present invention is used for thehole-injection layer of the light-emitting element. The results alsosuggest that a light-emitting element having a long lifetime can bemanufactured when the composite material of one embodiment of thepresent invention is used for the hole-injection layer.

The experimental results of the light-emitting element 9 in this exampleshow that the composite materials of embodiments of the presentinvention can be suitably used for a light-emitting element whichexhibits blue fluorescence.

Example 10

In this example, a light-emitting element of one embodiment of thepresent invention is described with reference to FIG. 26A. The materialsused in this example are the ones used in the above examples, andtherefore the chemical formulae thereof are omitted here.

The way how a light-emitting element 10 of this example was fabricatedis described below.

(Light-Emitting Element 10)

First, a film of ITSO was formed over a glass substrate 1100 by asputtering method, so that the first electrode 1101 which functions asan anode was formed. Note that the thickness was set to 110 nm and theelectrode area was set to 2 mm×2 mm.

In pretreatment for forming the light-emitting element over thesubstrate 1100, UV ozone treatment was performed for 370 seconds afterwashing of a surface of the substrate with water and baking that wasperformed at 200° C. for 1 hour.

After that, the substrate was transferred into a vacuum evaporationapparatus where the pressure had been reduced to approximately 10⁻⁴ Pa,and was subjected to vacuum baking at 170° C. for 30 minutes in aheating chamber of the vacuum evaporation apparatus, and then thesubstrate 1100 was cooled down for about 30 minutes.

Next, the substrate 1100 provided with the first electrode 1101 wasfixed to a substrate holder in the vacuum evaporation apparatus so thatthe surface over which the first electrode 1101 was provided faceddownward. The pressure in the vacuum evaporation apparatus was reducedto about 10⁻⁴ Pa. Then, P4N and molybdenum(VI) oxide were co-evaporatedto form the hole-injection layer 1111 over the first electrode 1101. Thethickness of the hole-injection layer 1111 was set to 40 nm, and themass ratio of P4N to molybdenum oxide was adjusted to 4:2(=P4N:molybdenum oxide).

Next, over the hole-injection layer 1111, a film of BPAFLP was formed toa thickness of 10 nm to form a hole-transport layer 1112.

Furthermore, 2mDBTPDBq-II, NPB, and [Ir(dppm)₂(acac)] were co-evaporatedto form a light-emitting layer 1113 over the hole-transport layer 1112.Here, the mass ratio of 2mDBTPDBq-II to NPB and [Ir(dppm)₂(acac)] wasadjusted to 0.8:0.2:0.05 (=2mDBTPDBq-II:NPB:[Ir(dppm)₂(acac)]). Inaddition, the thickness of the light-emitting layer 1113 was set to 40nm.

Further, over the light-emitting layer 1113, a film of 2mDBTPDBq-II wasformed to a thickness of 10 nm to form the first electron-transportlayer 1114 a.

Then, over the first electron-transport layer 1114 a, a film of BPhenwas formed to a thickness of 20 nm to form the second electron-transportlayer 1114 b.

Further, over the second electron-transport layer 1114 b, a film of LiFwas formed by evaporation to a thickness of 1 nm to form theelectron-injection layer 1115.

Lastly, an aluminum film was formed by evaporation to a thickness of 200nm as the second electrode 1103 functioning as a cathode. Thus, thelight-emitting element 10 of this example was fabricated.

Note that, in all the above evaporation steps, evaporation was performedby a resistance-heating method.

Table 17 shows element structures of the light-emitting element 10obtained as described above.

TABLE 17 First Second Hole- Hole- Light- electron- electron- Electron-First injection transport emitting transport transport injection Secondelectrode layer layer layer layer layer layer electrode Light- ITSOP4N:MoOx BPAFLP 2mDBTPDBq-II:NPB:[Ir(dppm)₂(acac)] 2mDBTPDBq-II BPhenLiF Al emitting 110 nm (=4:2) 10 nm (=0.8:0.2:0.05) 10 nm 20 nm 1 nm 200nm element 10 40 nm 40 nm

In a glove box containing a nitrogen atmosphere, the light-emittingelement 10 was sealed so as not to be exposed to the air. Then,operation characteristics of the light-emitting element 10 weremeasured. Note that the measurements were carried out at roomtemperature (in an atmosphere kept at 25° C.).

The luminance versus voltage characteristics of the light-emittingelement 10 are shown in FIG. 38. In FIG. 38, the horizontal axisrepresents voltage (V) and the vertical axis represents luminance(cd/m²). In addition, the current efficiency versus luminancecharacteristics of the element are shown in FIG. 39. In FIG. 39, thehorizontal axis represents luminance (cd/m²) and the vertical axisrepresents current efficiency (cd/A). Further, Table 18 shows thevoltage (V), CIE chromaticity coordinates (x, y), current efficiency(cd/A), and external quantum efficiency (%) of the light-emittingelement 10 at a luminance of 940 cd/m².

TABLE 18 External Chromaticity Current quantum Voltage coordinatesLuminance efficiency efficiency (V) (x, y) (cd/m²) (cd/A) (%) Light- 2.8(0.57, 0.42) 940 67 28 emitting element 10

As shown in Table 18, the CIE chromaticity coordinates of thelight-emitting element 10 are (x, y)=(0.57, 0.42) at a luminance of 940cd/m². This shows that orange light emission originating from[Ir(dppm)₂(acac)] was obtained from the light-emitting element 10.

As can be seen from FIG. 38 and FIG. 39, the light-emitting element 10has a low driving voltage and high emission efficiency. In addition, thelight-emitting element 10 is found to have an extremely high externalquantum efficiency at a luminance of 940 cd/m², which is 28%.

Next, the light-emitting element was subjected to a reliability test.Results of the reliability test are shown in FIG. 40. In FIG. 40, thevertical axis represents normalized luminance (%) with an initialluminance of 100% and the horizontal axis represents driving time (h) ofthe element.

In the reliability test, the light-emitting element of this example wasdriven under the conditions where the initial luminance was set to 5000cd/m² and the current density was constant.

FIG. 40 shows that the light-emitting element 10 kept 90% of the initialluminance after 330 hours elapsed. It is found that the light-emittingelement 10 to which one embodiment of the present invention is appliedhas a long lifetime and high reliability.

The above results suggest that an element having high emissionefficiency can be achieved when the composite material of one embodimentof the present invention is used for the hole-injection layer of thelight-emitting element which exhibits phosphorescence. The results alsosuggest that a light-emitting element having a low driving voltage canbe provided when the composite material of one embodiment of the presentinvention is used for the hole-injection layer of the light-emittingelement which exhibits phosphorescence. The results also suggest that alight-emitting element having a long lifetime can be manufactured whenthe composite material of one embodiment of the present invention isused for the hole-injection layer of the light-emitting element whichexhibits phosphorescence.

Further, the results suggest that the composite material of oneembodiment of the present invention can be suitably used for thehole-injection layer of the light-emitting element which exhibits orangephosphorescence. It is thus found that the composite material can besuitably used for a light-emitting element which exhibits orange lightor light having a longer wavelength than orange light.

Example 11

In this example, 9,9′-(biphenyl-3,3′-diyl)-di-phenanthrene(abbreviation: mPnBP), which is a hydrocarbon compound that can be usedfor the composite material of one embodiment of the present invention,is described. A structural formula of mPnBP is illustrated below.

Further, FIG. 41A shows an absorption spectrum of mPnBP in a toluenesolution of mPnBP, and FIG. 41B shows an emission spectrum thereof. Theabsorption spectrum was measured using an ultraviolet-visiblespectrophotometer (V-550, produced by JASCO Corporation). Themeasurements were performed in such a way that each solution was put ina quartz cell. Here is shown the absorption spectrum which was obtainedby subtraction of the absorption spectra of quartz and toluene fromthose of quartz and the solution. In FIG. 41A, the horizontal axisrepresents wavelength (nm) and the vertical axis represents absorptionintensity (arbitrary unit). In FIG. 41B, the horizontal axis representswavelength (nm) and the vertical axis represents emission intensity(arbitrary unit). Further, mPnBP exhibits an absorption peak at around282 nm, 298 nm, and 348 nm and an emission wavelength peak at 356 nm,373 nm, and 394 nm (at an excitation wavelength of 306 nm).

It is thus found from the absorption spectrum of mPnBP in a toluenesolution, that no absorption spectrum in the visible light region isobserved and therefore mPnBP is suitable as the hydrocarbon compoundused for the composite material of one embodiment of the presentinvention. In addition, since the emission peaks are located at theshorter wavelengths, the hydrocarbon compound is suitable for a materialof a hole-transport layer in contact with the light-emitting layer orfor a host material of a light-emitting layer.

Reference Example 1

A synthesis example in which3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN)used in the above example was prepared is described.

A synthesis scheme of PCPN is illustrated in (a-1).

In a 200 mL three-neck flask, a mixture of 5.0 g (15.5 mmol) of3-bromo-9-phenyl-9H-carbazole, 4.2 g (17.1 mmol) of4-(1-naphthyl)-phenylboronic acid, 38.4 mg (0.2 mmol) of palladium(II)acetate, 104 mg (0.3 mmol) of tri(ortho-tolyl)phosphine, 50 mL oftoluene, 5 mL of ethanol, and 30 mL of a 2 mol/L aqueous potassiumcarbonate solution was degassed while being stirred under reducedpressure, and reacted by being stirred and heated at 85° C. for 9 hoursunder a nitrogen atmosphere.

After the reaction, 500 mL of toluene was added to this reaction mixturesolution, and the organic layer of this mixture solution was filteredthrough Florisil (produced by Wako Pure Chemical Industries, Ltd.,Catalog No. 540-00135), alumina, and Celite (produced by Wako PureChemical Industries, Ltd., Catalog No. 531-16855). The obtained filtratewas washed with water, and magnesium sulfate was added thereto so thatmoisture was adsorbed. This suspension was filtered to obtain afiltrate. The obtained filtrate was concentrated and purified by silicagel column chromatography. At this time, a mixed solvent of toluene andhexane (toluene:hexane=1:4) was used as a developing solvent for thechromatography. The obtained fraction was concentrated, and methanol wasadded thereto. The mixture was irradiated with ultrasonic waves and thenrecrystallized to give 6.24 g of a white powder in a yield of 90%, whichwas the object of the synthesis.

This compound was identified as3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN),which was the object of the synthesis, by nuclear magnetic resonance(¹H-NMR) spectroscopy.

1H NMR data of the obtained substance are as follows: ¹H NMR (CDCl₃, 300MHz): δ (ppm)=7.30-7.35 (m, 1H), 7.44-7.67 (m, 14H), 7.76 (dd, J=8.7 Hz,1.8 Hz, 1H), 7.84-7.95 (m, 4H), 8.04 (d, J=7.8, 1H), 8.23 (d, J=7.8,1H), 8.46 (d, J=1.5, 1H).

Reference Example 2

A method of synthesizing2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation:2mDBTPDBq-II), which was used in the above examples, is described.

A synthesis scheme of 2mDBTPDBq-II is shown in (b-1).

First, 5.3 g (20 mmol) of 2-chlorodibenzo[f,h]quinoxaline, 6.1 g (20mmol) of 3-(dibenzothiophen-4-yl)phenylboronic acid, 460 mg (0.4 mmol)of tetrakis(triphenylphosphine)palladium(0), 300 mL of toluene, 20 mL ofethanol, and 20 mL of a 2M aqueous solution of potassium carbonate wereput in a 2 L three-neck flask. The mixture was degassed by being stirredunder reduced pressure, and the air in the three-neck flask was replacedwith nitrogen. This mixture was stirred under a nitrogen stream at 100°C. for 7.5 hours. After cooled to room temperature, the obtained mixturewas filtered to give a white residue. The obtained residue was washedwith water and ethanol in this order, and then dried. The obtained solidwas dissolved in about 600 mL of hot toluene, followed by filtrationthrough Celite and Florisil, so that a clear colorless filtrate wasobtained. The obtained filtrate was concentrated and purified by silicagel column chromatography using silica gel. The chromatography wascarried out using hot toluene as a developing solvent. Acetone andethanol were added to the solid obtained here, followed by irradiationwith ultrasonic waves. Then, the generated suspended solid was collectedby filtration and the obtained solid was dried, so that 7.85 g of awhite powder of the object of the synthesis was obtained in 80% yield.

By a train sublimation method, 4.0 g of the obtained white powder waspurified. In the purification, the white powder was heated at 300° C.under a pressure of 5.0 Pa with a flow rate of argon gas of 5 mL/min.After the purification, the object of the synthesis was obtained in ayield of 88% as 3.5 g of a white powder.

A nuclear magnetic resonance (′H NMR) spectroscopy identified thiscompound as 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline(abbreviation: 2mDBTPDBq-II), which was the object of the synthesis.

NMR data of the obtained substance are shown below.

¹H NMR (CDCl₃, 300 MHz): δ (ppm)=7.45-7.52 (m, 2H), 7.59-7.65 (m, 2H),7.71-7.91 (m, 7H), 8.20-8.25 (m, 2H), 8.41 (d, J=7.8 Hz, 1H), 8.65 (d,J=7.5 Hz, 2H), 8.77-8.78 (m, 1H), 9.23 (dd, J=7.2 Hz, 1.5 Hz, 1H), 9.42(dd, J=7.8 Hz, 1.5 Hz, 1H), 9.48 (s, 1H).

Reference Example 3

Reference Example 3 shows a method of synthesizingN,N′-bis(3-methylphenyl)-N,N′-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine(abbreviation: 1,6mMemFLPAPrn) used in the above Examples. Thestructural formula of 1,6mMemFLPAPrn is shown below.

Step 1: Synthesis Method of3-Methylphenyl-3-(9-phenyl-9H-fluoren-9-yl)phenylamine (abbreviation:mMemFLPA)

A synthesis scheme of Step 1 is illustrated in (c-1).

There were put 3.2 g (8.1 mmol) of 9-(3-bromophenyl)-9-phenylfluoreneand 2.3 g (24.1 mmol) of sodium tert-butoxide in a 200 mL three-neckflask. The air in the flask was replaced with nitrogen. Then, 40.0 mL oftoluene, 0.9 mL (8.3 mmol) of m-toluidine, and 0.2 mL of a 10% hexanesolution of tri(tert-butyl)phosphine were added to this mixture. Thetemperature of this mixture was set to 60° C., and 44.5 mg (0.1 mmol) ofbis(dibenzylideneacetone)palladium(0) was added to the mixture. Thetemperature of the mixture was raised to 80° C., followed by stirringfor 2.0 hours. After the stirring, the mixture was suction-filteredthrough Florisil, Celite, and alumina to give a filtrate. The filtratewas concentrated to give a solid, which was then purified by silica gelcolumn chromatography (with a developing solvent containing hexane andtoluene in a 1:1 ratio). Recrystallization was performed from a mixedsolvent of toluene and hexane. Accordingly, 2.8 g of a white solid ofthe object of the synthesis was obtained in 82% yield.

Step 2: Synthesis Method of 1,6mMemFLPAPrn)

A synthesis scheme of Step 2 is illustrated in (c-2).

There were put 0.6 g (1.7 mmol) of 1,6-dibromopyrene, 1.4 g (3.4 mmol)of mMemFLPA obtained in Step 1 above, and 0.5 g (5.1 mmol) of sodiumtert-butoxide in a 100 mL three-neck flask. The air in the flask wasreplaced with nitrogen. To this mixture were added 21.0 mL of tolueneand 0.2 mL of a 10% hexane solution of tri(tert-butyl)phosphine. Thetemperature of this mixture was set to 60° C., and 34.9 mg (0.1 mmol) ofbis(dibenzylideneacetone)palladium(0) was added to the mixture. Thetemperature of this mixture was set to 80° C., followed by stirring for3.0 hours. After the stirring, 400 mL of toluene was added to themixture, and the mixture was heated. While the mixture was kept hot, itwas suction-filtered through Florisil, Celite, and alumina to give afiltrate. The filtrate was concentrated to give a solid, which was thenpurified by silica gel column chromatography (with a developing solventcontaining hexane and toluene in a 3:2 ratio) to give a yellow solid.Recrystallization of the obtained yellow solid from a mixed solvent oftoluene and hexane gave 1.2 g of a yellow solid in 67% yield, which wasthe object of the synthesis.

By a train sublimation method, 1.0 g of the obtained yellow solid waspurified. In the purification, the yellow solid was heated at 317° C.under a pressure of 2.2 Pa with a flow rate of argon gas of 5.0 mL/min.After the purification, 1.0 g of a yellow solid of the object of thesynthesis was obtained in 93% yield.

A nuclear magnetic resonance (NMR) spectroscopy and a mass spectrometryidentified this compound asN,N′-bis(3-methylphenyl)-N,N′-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine(abbreviation: 1,6mMemFLPAPrn), which was the object of the synthesis.

¹H NMR data of the obtained compound is shown below.

¹H NMR (CDCl₃, 300 MHz): δ=2.21 (s, 6H), 6.67 (d, J=7.2 Hz, 2H), 6.74(d, J=7.2 Hz, 2H), 7.17-7.23 (m, 34H), 7.62 (d, J=7.8 Hz, 4H), 7.74 (d,J=7.8 Hz, 2H), 7.86 (d, J=9.0 Hz, 2H), 8.04 (d, J=8.7 Hz, 4H).

Reference Example 4

A synthetic example of(acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III)(abbreviation: [Ir(tBuppm)₂(acac)]), which was used in the aboveexamples, is described.

Synthesis of 4-tert-Butyl-6-phenylpyrimidine (abbreviation: HtBuppm)

A synthesis scheme of Step 1 is shown in (d-1) given below.

First, 22.5 g of 4,4-dimethyl-1-phenylpentane-1,3-dione and 50 g offormamide were put into a recovery flask equipped with a reflux pipe,and the air in the flask was replaced with nitrogen. This reactioncontainer was heated, so that the reacted solution was refluxed for 5hours. After that, this solution was poured into an aqueous solution ofsodium hydroxide, and an organic layer was extracted withdichloromethane. The obtained organic layer was washed with water andsaturated saline, and dried with magnesium sulfate. The solution afterdrying was filtered. The solvent of this solution was distilled off, andthen the obtained residue was purified by silica gel columnchromatography using hexane and ethyl acetate as a developing solvent ina volume ratio of 10:1, so that a pyrimidine derivative HtBuppm(colorless oily substance, yield of 14%) was obtained.

Step 2: Synthesis ofDi-μ-chloro-bis[bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III)](abbreviation: [Ir(tBuppm)₂Cl]₂)

A synthesis scheme of Step 2 is shown in (d-2) given below.

Next, 15 mL of 2-ethoxyethanol, 5 mL of water, 1.49 g of HtBuppmobtained in Step 1, and 1.04 g of iridium chloride hydrate (IrCl₃.H₂O)were put into a recovery flask equipped with a reflux pipe, and the airin the flask was replaced with argon. After that, irradiation withmicrowaves (2.45 GHz, 100 W) was performed for 1 hour to cause areaction. The solvent was distilled off, and then the obtained residuewas suction-filtered and washed with ethanol, so that a dinuclearcomplex [Ir(tBuppm)₂Cl]₂ (yellow green powder, yield of 73%) wasobtained.

Step 3: Synthesis of [Ir(tBuppm)₂(acac)]

A synthesis scheme of Step 3 is shown in (d-3) given below.

Further, 40 mL of 2-ethoxyethanol, 1.61 g of the dinuclear complex[Ir(tBuppm)₂Cl]₂ obtained in Step 2, 0.36 g of acetylacetone, and 1.27 gof sodium carbonate were put into a recovery flask equipped with areflux pipe, and the air in the flask was replaced with argon. Afterthat, irradiation with microwaves (2.45 GHz, 120 W) was performed for 60minutes to cause a reaction. The solvent was distilled off, and theobtained residue was suction-filtered with ethanol and washed with waterand ethanol. This solid was dissolved in dichloromethane, and themixture was filtered through a filter aid in which Celite (produced byWako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina,and Celite were stacked in this order. The solvent was distilled off,and the obtained solid was recrystallized with a mixed solvent ofdichloromethane and hexane, so that the object of the synthesis wasobtained as yellow powder (yield of 68%).

An analysis result by nuclear magnetic resonance (¹H NMR) spectroscopyof the yellow powder obtained in Step 3 is described below. Theseresults show that [Ir(tBuppm)₂(acac)] was obtained in this synthesisexample.

¹H NMR. δ (CDCl₃): 1.50 (s, 18H), 1.79 (s, 6H), 5.26 (s, 1H), 6.33 (d,2H), 6.77 (t, 2H), 6.85 (t, 2H), 7.70 (d, 2H), 7.76 (s, 2H), 9.02 (s,2H).

Reference Example 5

A synthetic example of an organometallic complex(acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III)(abbreviation: [Ir(dppm)₂(acac)]), which was used in the above examples,is described.

Step 1: Synthesis of 4,6-Diphenylpyrimidine (abbreviation: Hdppm)

First, 5.02 g of 4,6-dichloropyrimidine, 8.29 g of phenylboronic acid,7.19 g of sodium carbonate, 0.29 g ofbis(triphenylphosphine)palladium(II)dichloride (abbreviation:Pd(PPh₃)₂Cl₂), 20 mL of water, and 20 mL of acetonitrile were put into arecovery flask equipped with a reflux pipe, and the air in the flask wasreplaced with argon. This reaction container was heated by irradiationwith microwaves (2.45 GHz, 100 W) for 60 minutes. Here, there werefurther put 2.08 g of phenylboronic acid, 1.79 g of sodium carbonate,0.070 g of Pd(PPh₃)₂Cl₂, 5 mL of water, and 5 mL of acetonitrile intothe flask, and the mixture was heated again by irradiation withmicrowaves (2.45 GHz, 100 W) for 60 minutes. After that, water was addedto this solution and an organic layer was extracted withdichloromethane. The obtained solution of the extract was washed withwater and dried with magnesium sulfate. The solution after drying wasfiltered. The solvent of this solution was distilled off, and then theobtained residue was purified by silica gel column chromatography usingdichloromethane as a developing solvent, so that a pyrimidine derivativeHdppm (yellow white powder, yield of 38%) was obtained. Note that forthe microwave irradiation, a microwave synthesis system (Discover,manufactured by CEM Corporation) was used. A synthesis scheme (e-1) ofStep 1 is illustrated below.

(Step 2: Synthesis ofDi-μ-chloro-bis[bis(4,6-diphenylpyrimidinato)iridium(III)](abbreviation: [Ir(dppm)₂Cl]₂)

Next, 15 mL of 2-ethoxy ethanol, 5 mL of water, 1.10 g of Hdppm obtainedin Step 1, and 0.69 g of iridium chloride hydrate (IrCl₃.H₂O) were putinto a recovery flask equipped with a reflux pipe, and the air in therecovery flask was replaced with argon. After that, irradiation withmicrowaves (2.45 GHz, 100 W) was performed for 1 hour to cause areaction. The solvent was distilled off, and then the obtained residuewas filtered and washed with ethanol to give a dinuclear complex[Ir(dppm)₂Cl]₂ (reddish brown powder, yield of 88%). A synthesis scheme(e-2) of Step 2 is illustrated below.

Step 3: Synthesis of(Acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III)(abbreviation: [Ir(dppm)₂(acac)])

Furthermore, 40 mL of 2-ethoxyethanol, 1.44 g of [Ir(dppm)₂Cl]₂ obtainedin Step 2, 0.30 g of acetylacetone, and 1.07 g of sodium carbonate wereput into a recovery flask equipped with a reflux pipe, and the air inthe recovery flask was replaced with argon. After that, irradiation withmicrowaves (2.45 GHz, 120 W) was performed for 60 minutes to cause areaction. The solvent was distilled off, the obtained residue wasdissolved in dichloromethane, and filtration was performed to removeinsoluble matter. The obtained filtrate was washed with water and thenwith saturated saline, and was dried with magnesium sulfate. Thesolution after drying was filtered. The solvent of this solution wasdistilled off, and then the obtained residue was purified by silica gelcolumn chromatography using dichloromethane and ethyl acetate as adeveloping solvent in a volume ratio of 50:1. After that,recrystallization was carried out with a mixed solvent ofdichloromethane and hexane, so that an orange powder (yield of 32%),which was the object of the synthesis, was obtained. A synthesis scheme(e-3) of Step 3 is illustrated below.

An analysis result by nuclear magnetic resonance (¹H NMR) spectroscopyof the orange powder obtained in Step 3 above is described below. Theseresults show that [Ir(dppm)₂(acac)] was obtained in this synthesisexample.

¹H NMR. δ (CDCl₃): 1.83 (s, 6H), 5.29 (s, 1H), 6.48 (d, 2H), 6.80 (t,2H), 6.90 (t, 2H), 7.55-7.63 (m, 6H), 7.77 (d, 2H), 8.17 (s, 2H), 8.24(d, 4H), 9.17 (s, 2H).

This application is based on Japanese Patent Application Serial No.2011-064629 filed with the Japan Patent Office on Mar. 23, 2011 andJapanese Patent Application Serial No. 2011-122829 filed with the JapanPatent Office on May 31, 2011, the entire contents of which are herebyincorporated by reference.

What is claimed is:
 1. A composite material comprising: a hydrocarbon compound having a skeleton selected from a naphthalene skeleton, a phenanthrene skeleton, and a triphenylene skeleton, and an inorganic compound, wherein the skeleton is bonded to a substituent having one or more rings selected from a benzene ring, a naphthalene ring, a phenanthrene ring, and a triphenylene ring, wherein a molecular weight of the hydrocarbon compound is greater than or equal to 350 and less than or equal to 2000, and wherein the hydrocarbon compound have an absorption peak at a shorter wavelength than a visible-light wavelength. 